IAOe?IIAEUeIA AEAAeAI?ss IAOE OE?A?IE

?INOEOOO I?AAI?*II? O?I??

OAeE 547.241’77’398.5’291+547.88.241

IOIANUeEEE Aaiiaae?e Aai?ai?iiae/

OINOI?EETHAAIIss N-ACIE?EOI?IAI?AeEI?A

02.00.08 – O?I?ss AEAIAIOII?AAI?*IEO NIIEOE

Aaoi?aoa?ao

aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy

eaiaeeaeaoa o?i?/ieo iaoe

Ee?a-1999

Aeena?oaoe??th ? ?oeiien.

?iaioa aeeiiaia o a?aeae?e? o?i?? oinoi?i?aai?/ieo niieoe ?inoeoooo
i?aai?/ii? o?i?? Iaoe?iiaeueii? Aeaaeai?? Iaoe Oe?a?ie.

Iaoeiaee ea??aiee: aeieoi? o?i?/ieo iaoe, i?ioani? I?i/oe Ieaenaiae?
Ieoaeeiae/, caa?aeoaa/ a?aeae?eo; ?inoeooo i?aai?/ii? o?i?? IAI Oe?a?ie,
i. Ee?a.

Io?oe?ei? iiiiaioe: aeieoi? o?i?/ieo iaoe, i?ioani? Aieiaaiei THe?ai
Ieoaeeiae/, eaoaae?a i?aai?/ii? o?i??, Ee?anueeee iaoe?iiaeueiee
oi?aa?neoao ?i. Oa?ana Oaa/aiea, i. Ee?a.

aeieoi? o?i?/ieo iaoe, i?ioani? TH?/aiei ?a?na ?aai?aia, eaoaae?a
i?aai?/ii? o?i??, Iaoe?iiaeueiee oaoi?/iee oi?aa?neoao “Ee?anueeee
iie?oaoi?/iee ?inoeooo”, i. Ee?a.

I?ia?aeia onoaiiaa: ?inoeooo a?ii?aai?/ii? o?i?? ? iaooio?i?? IAI
Oe?a?ie, a?aeae?e oiieiai i?aai?/iiai neioaco, i. Ee?a.

Caoeno aeena?oaoe?? a?aeaoaeaoueny “ 16 ” aa?aniy 1999?. i
10 aiaeei? ia can?aeaii? Niaoe?ae?ciaaii? a/aii? ?aaee Ae 26.217.01 i?e
?inoeooo? i?aai?/ii? o?i?? IAI Oe?a?ie ca aae?anith: 252660, i. Ee?a,
aoe Io?iainueea, 5.

C aeena?oaoe??th iiaeia iciaeiieoenue a iaoeia?e a?ae?ioaoe? ?inoeoooo
i?aai?/ii? o?i?? IAI Oe?a?ie.

Aaoi?aoa?ao ?ic?neaiee “ 13 ” na?iiy 1999?.

A/aiee nae?aoa? Niaoe?ae?ciaaii? a/aii? ?aaee

aeieoi? o?i?/ieo iaoe, i?ioani? Oauaiei
I. A.

ANOOI

Aeooaeuei?noue oaie. Neioac oa aeanoeaino? N-oinoi?eeueiaaieo ai?aeei?a
aeine?aeaeothoueny iiiaae o?e aeanyoee?ooy. Aeai? ia’?eoe aeyaeeeny
ei?enieie ye aeey oai?aoe/ieo aeine?aeaeaiue (oinoi?io?ii?y,
i?aeiieaeoey?i? i?a?aoe??, aaoa?ioeeee?caoe??), oae ? aeey i?aeoe/iiai
aeei?enoaiiy (ianoeoeeaee). Caeiiii??iei aoaiii i?e aeine?aeaeaii?
oinoi?eeueiaaieo ai?aeei?a aeyaeany ia?ao?ae a?ae N- aei
N-oinoi?eeueaaieo ai?aeei?a. Aea ne?ae cacia/eoe, ui a a?eueoino? ?ia?o,
i?enay/aieo N-oinoi?eeueiaaiei ai?aeeiai, ?icaeyaeathoueny nenoaie, a
yeeo oinoi?ia ooieoe?y ciaoiaeeoueny a?ey oi?iai?aeeiiaiai aoaeaoeaaiai
aoiia. Eeoa inoaii?i /anii, i?e ?aaeoe?? aaeiaai?ae?a o?eaaeaioiiai
oinoi?o c aeayeeie N1,N1-aeeia-oee-N2-a?eeoi?iai?aeeiaie, aoee io?eiai?
aeae?eueea i?aaenoaaiee?a o?ecai?uaieo oi?iai?aeei?a, oinoi?eeueiaaieo
ia a?ey oi?iai?aeeiiaiai aoiia aoaeaoeth, a a a?eeueiee caeeoie.
N-Oin-oi?eethaaiiy N1,N1-aeeiaoee-N2-aaoa?eeoi?iai?aeei?a aei aeaii?
?iaioe aoei iaa?aeiia. Iaeiae, aacoth/enue ia aeaeo?iiiaeiii?ieo
aeanoeainoyo ai?aeeiiaiai cai?nieea ? cia/i?e o?aini?n?? aeaeo?iiieo
aoaeo?a aaoa?ioeeee?/ieie nenoaiaie, iiaeia aoei i/?eoaaoe, ui
N1,N1-aeeiaoee-N2-aaoa?eeoi?iai?aeeie, ia a?aei?io a?ae
N1,N1-aeeiaoee-N2-a?eeoi?iai?aeei?a, aoaeooue oinoi?eethaaoeny ii
aaoa?ioeeee?/iiio caeeoeo. Nenoaie, aei neeaaeo yeeo iaeii/anii
aoiaeyoue oinoi?ia oa ai?aeeiiaa ooieoe??, ? oe?eaaeie caaaeyee ?yaeo
iioaioe?eii ei?enieo aeanoeainoae. Oe? nenoaie, a?aoiaoth/e
aeaeo?io?euei?noue ai?aeeiiaiai cai?nieea, iiaeooue aooe ia?aoai?ai? a
?io? niieoee: ai?aeeie (ia?aai?ioaaiiyi), aai a i?eioeeiiai aaaeeea?
N-oinoi?eeueiaai? ai?iiaaoa?ioeeeee – a?ae?ie?cii. Iniaeeai
ia?niaeoeaiei oyaey?oueny aeine?aeaeaiiy iiaeeeainoae
aioo??oiueiiieaeoey?iiai cai?uaiiy ioeeaio?eueiith oinoi?iith ooieoe??th
a?ey oi?iai?aeeiiaiai aoaeaoeaaiai aoiia c iaoith neioaco iiaeo
oinoi?iai?nieo aaoa?ioeeee?/ieo niieoe, ine?eueee oaeee i?aeo?ae ia?
aaaaoi aiaeia?e a i?aai?/i?e o?i??. Iaea?aeai? N-oinoi?e-eueiaai?
ai?aeeie iiaeooue oaeiae aeyaeoeny ei?enieie a i?eeeaaeieo aniaeoao,
ine?eueee aaaaoi N1,N1-aeeiaoee-N2-aaoa?eeoi?iai?aeei?a iathoue
aa?a?oeeaei?, ooia?oeeaei? oa ?io? aeaee ianoeoeeaeii? aeoeaiino?.

Iaoa ?iaioe. Aeine?aeaeaiiy oinoi?eethaaiiy
N1,N1-aeeiaoee-N2-acie?eoi?iaieaeei?a aaeiaai?aeaie o?eaaeaioiiai
oinoi?o. Aea/aiiy iiaeeeaino? aeei?enoaiiy
3-iaoee-1,3-ae?acaaoo-1-?i?eueiiai (ai?aeeiiaiai) cai?nieea ye caoenii?
a?oie ? ye eiiiiiaioa i?e iiaoaeia? oinoi?iai?nieo aaoa?ioeeee?a.

Iaoeiaa iiaecia. Ciaeaeaii oa i?aia?aoeaii ?ic?iaeai? iaoiaee
N-oinoi?eethaaiiy N1,N1-aeeiaoee-N2-acie?eoi?iai?aeei?a ii
aaoa?ioeeee?/iiio caeeoeo. Anoaiiaeaii, ui
3-iaoee-1,3-ae?acaaoo-1-?i?eueiee cai?niee ? neeueiei aeoeaaoi?ii i?e
oinoi?eethaaii? N1,N1-aeeiaoee-N2-acie?eoi?iai?aeei?a, iio?aeieo o?acieo
oa i??acieo, a oaeiae neoaeeoue caoeniith a?oiith ai?ii- oa oi?iai?aeii?
ooieoe?e a ?aaeoe?? aeaeo?io?eueiiai oinoi?eethaaiiy aaoa?ioeeee?/ieo
niieoe.

Cai?iiiiiaaii iiaee i?aeo?ae aei iiaoaeiae oinoi?iai?nieo
aaoa?ioeeee?/ieo niieoe, ui aaco?oueny ia aaaaoiooieoe?iiaeueiino?
ai?aeeiiaiai cai?nieea, yeee aenooia? aeoeaaoi?ii i?e aaaaeaii?
oinoi?iiai cai?nieea ? aa?a o/anoue a oeeeeiooai?aii? caaaeyee
aioo??oiueiiieaeoey?i?e aca?iiae?? c ioeeaio?eueiith oinoi?iith
ooieoe??th. Neioaciaaii iia? aaoa?ioeeee?/i? nenoaie:
i??aciei[4,5-e]-1,3,45-ae?acaoino?i?i e i??aciei[5,4-b]-
1,45-acaoino?i?i.

Ai?iaaoe?y ?iaioe. Iniiai? ?acoeueoaoe aoee i?aaenoaaeai? ia XIV
I?aeia?iaei?e eiioa?aioe?? c o?i?? oinoi?o (Oeeioe?iao?, Iaaei, NOA,
1998p.), I?aeia?iaei?e eiioa?aioe?? c o?i?? oa aeei?enoaiiy oinoi?-
n??ea- oa e?aii?ei?aai?/ieo niieoe “Iaoa?ao?aneea ano?a/e-98”
(Naieo-Iaoa?ao?a, 1998p.), XVIII Oe?a?inuee?e eiioa?aioe?? c i?aai?/ii?
o?i?? (Aei?i?iiao?iane, 1998p.), Ana?in?enuee?e eiioa?aioe?? “Oeiey
oinoi?i?aaie/aneeo niaaeeiaiee e ia?niaeoeau aa ?acaeoey ia ii?iaa XXI
aaea”, ui i?enay/aia iai’yo? I. ?. Eaaa/ieea (Iineaa, 1998p.),
Oe?a?inuee?e eiioa?aioe?? “O?i?y acioiai?nieo aaoa?ioeeee?a” (Oa?e?a,
1997p.).

Ioae?eaoe??. Ca iaoa??aeaie aeena?oaoe?eii? ?iaioe iioae?eiaaii 5
noaoae.

No?oeoo?a oa ianya aeena?oaoe??. Aeena?oaoe?y aeeeaaeaia ia 150
noi??ieao ? neeaaea?oueny ?c anooio, o?ueio ?icae?e?a, aeniiae?a, nieneo
e?oa?aoo?e, ui i?noeoue 200 iaeiaioaaiue, oa aeiaeaoe?a.

O ia?oiio ?icae?e? ocaaaeueiaii oa nenoaiaoeciaaii e?oa?aoo?i? aeai?,
i?enay/ai? aaoa?ioeeee?caoe?yi N1,N1-aeecai?uaieo N2-a?ee- e
N2-aaoa?eeoi?iai?aeei?a. Aeani? aeine?aeaeaiiy aaoi?a aeeeaaeaii a
ianooiieo aeaio ?icae?eao.

O ae?oaiio ?icae?e? a?aeia?aaeai? ?acoeueoaoe aeine?aeaeaiue,
i?enay/aieo N-oinoi?eethaaiith N1,N1-aeeiaoee-N2-acie?eoi?i-ai?aeei?a, o
o?aoueiio – iienai? aeanoeaino? iaea?aeaieo oinoi?eeueiaaieo nenoai:
?aaeoe??, ui i?io?eathoue c ?ic?eaii N-? ca’yceo, caoeni? aeanoeaino?
ai?aeeiiaiai cai?nieea oa aaoa?ioeeee?caoe??.

Eiie?aoiee iniaenoee aianie aeena?oaioa. Aenia?eiaioaeueia /anoeia
?iaioe, aiae?c niaeo?aeueieo aeine?aeaeaiue oa aeniiaee uiaei aoaeiae
neioaciaaieo niieoe cae?eniaii iniaenoi caeiaoaa/ai.

2. INIIAIEE CI?NO ?IAIOE.

2.1 ACA?IIAe?ss N-ACIE?EOI?IAI?AeEI?A C AAEIAAI?AeAIE O?EAAEAIOIIAI
OINOI?O.

N-Oinoi?eethaaiiy N1,N1-aeeiaoee-N2-aaoa?eeoi?iai?aeei?a ?ai?oa ia
aeine?aeaeoaaeinue. I?ioa, aa?o/e aei oaaae aeai? i?i aeaeo?iiiaeiii?i?
aeanoeaino? ai?aeeiiai? ooieoe?? oa aacoth/enue ia ?iaioao, i?enay/aieo
N-oinoi?eethaaiith aaoa?ioeeee?/ieo niieoe, iiaeia aoei niiae?aaoenue,
ui a ?acoeueoao? aeaeo?io?eueiiai oinoi?eethaaiiy
N1,N1-aeeiaoee-N2-aaoa?eeoi?iai?aeei?a oinoi?ia ooieoe?y aoaea
aaiaeeoeny aei aaoa?ioeeeeo, a ia aei ai?aeeiiaiai cai?nieea.

A?aeiii, ui aeey acie?a ? oa?aeoa?ieie aeaa i?eioeeiiai ??cieo
iaoai?cie aeaeo?io?eueiiai cai?uaiiy: aaoa?ia?aiii??aee oa ?e?aeiee;
naia oiio, aeey nenoaiiiai aiae?co i?iaeaie aeaeo?io?eueiiai
oinoi?eethaaiiy acie?eai?aeei?a ne?ae aoei aea?aoe i?aaenoaaieee
eiaeiiai oeio. sse iiaeaeuei? aoee aea?ai?
N1,N1-aee-iaoee-N2-acie?eoi?iai?aeeie – iio?aei? /ioe?ueio nenoai:
i??acieo 2.4, o?acieo 2.5 (aaoa?ia?aiii??aee iaoai?ci), o?eacieo 2.6 oa
o?aae?acieo 2.7 (?e?aeiee iaoai?ci).

I??acie?eoi?iai?aeei 2.4 oinoi?eeth?oueny o?eoei?eaeii oinoi?o a
iniiaiiio na?aaeiaeu? ii aaoa?ioeeee?/iiio caeeoeo c ooai?aiiyi
aeeoei?oino?io 2.9 c aenieei aeoiaeii. Oinoi?eethaaiiy niieoee 2.4
i?io?ea? cia/ii eaaoa, i?ae 5-Ia ? 5-IaI i??acie?a, aeine?aeaeaieo
?ai?oa (A. ?. Eiiiaaoeue N-Oinoi?e-eueiaai? i??aciee. Aeen. eaiae. o?i
iaoe: 02.00.08 – Ee?a, 1996).

Caaaeyee aenie?e ?aaeoe?ei?e caeaoiino? i??acie?eai?aeeio 2.4, eiai
iiaeii oinoi?eethaaoe oaeei iaei?aaeoe?eiicaeaoiei oino?iii, ye
aeeoai?eoei?oino?i, a oaeiae aaanoe aeaa /e o?e aaoa?ioeeee?/i? caeeoee
aei iaeiiai aoiia oinoi?o.

N-Oinoi?eethaaiiy iaio aeoeaieo o?acie?eoi?iai?aeei?a 2.5 a (R = H),
2.5 b (R = Ph) i?iaiaeeee o?ea?ii?aeii oinoi?o a i??eaeei? i?e
oaiia?aoo?? 20IN (/an ?aaeoe??: 4 aiae. (R = H), 8 aiae. (R = Ph)).
Oinoi?ia ooieoe?y aaiaeeoueny ia aei ai?aeeiiaiai cai?nieea, a a
/aoaa?oa iieiaeaiiy o?acieueiiai e?eueoey.

I?e oinoi?eethaaii? N1,N1-aeeiaoee-N2-(2-o?acie?e)-oi?iai?aeeio 2.5 a
aei iaeiiai aoiia oinoi?o iiaeia eaaei aaanoe o?e o?acieueieo caeeoea
(31? oino?io 2.29 = -60,41 i. ae., JPH = 4,8 Aoe).

E?euee?ni? aeai?, ui oa?aeoa?ecothoue aeaeo?iiiaeiii?i? aeanoeaino?
ai?aeeiiaiai cai?nieea, ae?aaeai? eeoa p eiinoaioith, ui aei??aith?
-0,250,1 (Raczynska E. D., Drapala T., J. Chem. Research (S), 1993,
54-55). Aeoiaey/e c niaeo?aeueieo aeaieo (13N ssI?), iaie ia/eneaii ?
eiinoaioo –N=CH–NMe2 cai?nieea, ui aei??aith? 0,6662. Oaeei /eiii, eiai
aeoeaoth/a caeaoi?noue aeecueea aei oaei? o ai?iia?oie. Aeai? uiaei
aeaeo?iiieo oa?aeoa?enoee ?ioeo i?aaenoaaiee?a ?yaeo
3-iaoee-1,3-ae?acaaoo-1-?i?eueiiai cai?nieea, oiaoi ?ioeo
oi?iai?aeeiiaeo cai?niee?a, ui ia iathoue iacai?uaii? NH ooieoe??, a
e?oa?aoo?? ia i?aaenoaaeai?. Naia oiio, aeei?enoiaoth/e iiaeeeaino? 31P
ssI? niaeo?ineii??, aoei i?iaaaeaii ye?nia ii??aiyiiy ?yaeo
o?acie?eoi?iai?aeei?a a ?aaeoe?? c o?eoei?eaeii oinoi?o a i??eaeei? ca
i?enooiino? o?eaoeeai?io.

Iaea?aeai? ?acoeueoaoe aeacothoue ia ianooiiee ii??aiyeueiee ?yae
aeoeaiino? oi?iai?aeeiiaeo ooieoe?e:

Ii??aiyiiy aeaco? ia neiaaoi?noue aeaeo?iiiaeiii?iiai aieeao aoi?eiieo
ai?i?a, ui ciaoiaeyoueny a?ey oi?iai?aeeiiaiai oeaio?o oa
oi?iai?aeeiiaeo cai?niee?a a oe?eiio.

Ianooii? iiaeaeuei? nenoaie:
N1,N1-aeeiaoee-N2-2-(1,3,4-o?aae?acie?e)oi?iai?aeei 2.7 oa
N1,N1-aeeiaoee-N2-4-(1,2,4-o?eacie?e)oi?iai?aeei 2.6 aeyaeeeny
aeniei?aaeoe?eiicaeaoieie noano?aoaie a ?aaeoe?? aeaeo?io?eueiiai
oinoi?eethaaiiy. Aiie eaaei oinoi?eeththoueny a?ey aaoa?ioeeeeo ia eeoa
oei?oino?iaie, aea e oaeeie iaei?aaeoe?eiicaeaoieie N-oinoi?eethth/eie
?aaaaioaie ye ai?aeioei?oino?oe.

Ne?ae cacia/eoe, ui ?aaeoe?eia caeaoi?noue o?aae?acie?eoi?iai?aeeio 2.7
cia/ii aeua, i?ae o aiaeia?/iiai iio?aeiiai o?acieo:
N1,N1-aeeiaoee-N2-2-o?acie?eoi?iai?aeeio 2.5, ui a?aeaeaa?oueny a
iiaeeeaino? aeei?enoaiiy aeey oinoi?eethaaiiy a?eueo neaaeeo ?aaaaio?a
oa iaioi? o?eaaeino? ?aaeoe??. Cia/ia ca?eueoaiiy ?aaeoe?eii? caeaoiino?
i?e ia?aoiae? a?ae iio?aeiiai o?acieo aei o?aae?acieo, ui ia
ocaiaeaeo?oueny c cia/iei cieaeaiiyi aeaeo?iiii? aonoeie a 5-io
iieiaeaii? aaoa?ioeeeeo ca ?aooiie aeaeo?iiiaeoeaioi?iiai aieeao
aeiaeaoeiaiai i??eaeeiiaiai aoiia acioo, i/aaeaeii, iaoiiaeaia ??cieie
iaoai?ciaie aeaeo?io?eueiiai cai?uaiiy: o aeiaaeeo iio?aeiiai o?acieo
2.5 – aaoa?ia?aiii??aiai, a aeey o?aae?acie?eai?aeeio 2.7 – ?e?aeiiai.

Iaea?aeaiei aaeiaaioino?iai 2.9, 2.26 aeanoea? oeiia? ?ene ?aaeoe?eii?
iiaaae?iee aaoa?eeaaeiaaioino?i?a. Oae, ?aaeoe?? ?c nie?oaie oa ai?iaie
i?eaiaeyoue aei a?aeiia?aeieo anoa??a oa ai?ae?a eeneio o?eaaeaioiiai
oinoi?o. Ieeniaiiy inoaii?o ia?aeenii aiaeith, aai ?aaeoe?y c n??eith /e
aceaeaie aaaea aei ieni-, o?i- /e ?i?iiiio?aeieo a?aeiia?aeii.

Oaeei /eiii, ca?aeii c iaoei i?eiouaiiyi, aeey
N1,N1-aee-iaoee-N2-a?eeoi?iai?aeei?a oa
N1,N1-aeeiaoee-N2-aaoa?eeoi?i-ai?aeei?a niinoa??aa?oueny ??cia
iiaaae?iea a ?aaeoe?? aeaeo?io?eueiiai oinoi?eethaaiiy: ia?o?
oinoi?eeththoueny ii oi?iai?aeeiiaiio aoiio aoaeaoeth, ae?oa? – ii
aaoa?ioeeeeo.

Oai?aoe/iee oa i?aia?aoeaiee ?ioa?an iaei aeine?aeaeaiiy oinoi?eethaaiiy
aaeiaai?aeaie o?eaaeaioiiai oinoi?o N,N’-aee-cai?uaieo oi?iai?aeei?a
2.61, ye iioaioe?eieo N,C-a?ooieoe?iiaeue-ieo niieoe, aeey yeeo iiaeia
aoei i/?eoaaoe iaeii/anii c eeane/iei cai?uaiiyi a?ey aoiia acioo,
oinoi?eethaaiiy oi?iai?aeeiiaiai aoiia aoaeaoeth /e aaoa?eeueiiai
(a?eeueiiai) caeeoeo. Aea aeyaeeinue, ui i?e oinoi?eethaaii?
N,N’-aeecai?uaieo oi?iai?aeei?a a ?aaeoe?? aa?ooue o/anoue eeoa aoii
acioo oa oi?iai?aeeiiaee aoii aoaeaoeth. Ca ia?aoai?aiiyi 2.61 2.63
eaaei niinoa??aaoe ca aeiiiiiaith 31? ssI? niaeo??a: ca oaeaeeei
ooai?aiiyi ca’ceo i?ae oinoi?ii oa oi?iai?aeeiiaei aoiiii acioo ne?aeo?
aeeia?ecaoe?y, ui o?eaa? 5-7 aiaeei ? i?eaiaeeoue aei
1,4,2,5-ae?aca-aeeoinoi?eiai?a. Aeoiaey/e c P-Cl niieoe 2.63 iaea?aeai?
cai?uai? 1,4,2,5-ae?acaaeeoinoi?eiaie 2.64.

Oey iiaa aaoa?ioeeee?caoe?y aeine?aeaeoaaeanue ia i?eeeaae? ?yaeo ye
aaoa?ee-, oae ? a?eeoi?iai?aeei?a. Iaea?aeai?
1,4,2,5-ae?aca-aeeoinoi?eiaie iiaeooue ?nioaaoe o aeaeyae? cis- oa
trans-?ciia??a, a caeaaeiino? a?ae i?inoi?iaiai ?ici?uaiiy cai?niee?a
a?ey aoiia oinoi?o.

Iaeaeaa ?ciia?e (cis- oa trans-) cia/iith i??ith i?inoi?iai
ia?aaaioaaeai?. Aeoiaey/e c cia/iiai ooe?aiiy a II? niaeo?ao neaiae?a,
ui a?aeiia?aeathoue cai?nieeai, aaciina?aaeiuei ca’ycaiei c e?eueoeai,
iiaeia c?iaeoe aeniiaie, ui ??cieoey aia?a?e i?ae eiioi?ia?aie eiaeiiai
c ?ciia??a iacia/ia. Oea caeiiii??ii, ine?eueee iaea?aeai?
1,4,2,5-ae?acaaeeoinoi?eiaie iathoue aeaa sp2-a?a?e-aeeciaai? aoiie
aoaeaoeth a e?eueoe?. Naia oiio niinoa??aa?oueny aeeiai?/ia ??aiiaaaa
eiioi?ia??a cai?noue ia?aaaaeaiiy iaeiiai, ui ? oa?aeoa?iei aeey iaio
i?inoi?iai ia?aaaioaaeaieo oinoaaaoa?i-aiaeueiaaieo oeeeeiaaenai?a.

O aeiaaeeo niieoe 2.65 a, a’ oa 2.64 n, c’ iaeaeaa ?ciia?e aoee
aeae?eai? caaaeyee ??ci?e ?ic/eiiino?. ?aioaaiino?oeoo?iee aiae?c
i?aeoaa?aeea no?oeoo?o 2.65 a’, a e?enoae?/iiio noai? oeae ?ciia? ?nio?
a eiioi?iaoe?? aaiie (?en. 1).

?en. 1. 1,4,2,5-Ae?acaaeeoinoi?eiai 2.65 a’.

2.2 AEANOEAINO? N-OINOI?EEUeIAAIEO

N-ACIE?EOI?IAI?AeEI?A

A?aeiii, ui i?oei?noue N-? ca’yceo cieaeo?oueny i?e i?aeaeuaii?
/anoeiaiai iaaaoeaiiai ca?yaeo ia aoii? aoaeaoeth, ui ca’ycaiee c
oinoi?ii. Naia oiio aeyaeeinue i?eioeeiiaei aeine?aeeoe aieea
aeaeo?iiiaeiii?ii? 3-iaoee-1,3-ae?acaaoo-1-?i?eueii? ooieoe?? ia
i?oei?noue ca’yceo oinoi?-aoaeaoeue a N-oinoi?eeueiaaieo
N-acie?e-oi?iai?aeeiao.

O aeiaaeeo oei?oino?io 2.12 N-? ca’ycie eaaei i?io?ea? i?ae ae??th
o?eoei?eaeo oinoi?o a i??eaeei?, ui ciaoiaeeoue aeyaeaiiy a
neiao?ecaoe?? 2.122.9.

Ca’ycie ai?aeeiii??acieueiiai caeeoeo c i’yoeaaeaioiith oinoi?iith
ooieoe??th oaeiae iaaiith i??ith iao?eaeee, aea aeey eiai ?ic?eao
iio??ai? cia/ii aei?noe?o? oiiae. Oae, aeey ?aae?caoe?? oeueiai
ia?aoai?aiiy iaiao?aeia iaa??aaiiy i?e oaiia?aoo?? eei?iiy a
eiioeaio?iaaiiio ?ic/ei? nieyii? eeneioe i?ioyaii aiaeeie.

Oino?ie 2.46 oa 2.44, ui iathoue no?ee? N-? ca’ycee a oiiaao eoaeiiai
a?ae?ie?co, c?o/ii ia?aoai?ththoueny a ai?iiaaoa?eeoino?ie 3.7 oa 3.8,
iayai?noue a yeeo e?eueeio ooieoe?iiaeueieo a?oi a?aee?eaa? oe?ie?
ia?niaeoeae aeey ?o iiaeaeueoiai neioaoe/iiai aeei?enoaiiy.

Caaaeyee eoaeiiio a?ae?ie?co
2-(3-iaoee-1,3-ae?acaaoo-1-?i?e)-4-oai?e-5-o?acie?eoinoii?noi? eeneioe
2.30 aoea iaea?aeaia iao???aa n?eue ai?iio?acie?eoinoii?noi? eeneioe
3.13.

Ai?aeeiiaee caoeno aeyaeany c?o/iei a neioac? ai?iiaaoa?ioeeee?a, ui
i?noyoue PV oinoi?i? ooieoe??. Oino?iieneaee, ae?ai?aeioinoiiaoe oa
ae?aee?eoinoiiaoe, a oaeiae ?oi? o?iiene-aiaeiae, iio?aei?
3-iaoee-1,3-ae?acaaoo-1-?i?ecai?uaieo o?acieo oa o?aae?acieo a oiiaao
eoaeiiai a?ae?ie?co ia?aoai?ththoueny o a?aeiia?aei? N-oinoi?eeueiaai?
ai?iiaaoa?ioeeeee c aenieei aeoiaeii.

Iaci?ii?noue oi?iai?aeeiiai? ooieoe?? i?e aeaeo?io?eueiiio
oinoi?eethaaii? N1,N1-aeeiaoee-N2-acie?eoi?iai?aeei?a, a oaeiae
eaae?noue ?? ia?aoai?aiiy a ai?ii- /e oi?iai?aeio ooieoe?? a oiiaao
eoaeiiai aai eeneiai a?ae?ie?co a?aeiia?aeii, coiiaeththoue
ia?niaeoeai?noue ?? aeei?enoaiiy a yeino? caoenii? i?e oinoi?eethaaii?
aaoa?ioeeee?/ieo niieoe, aea eeane/iee aoeaoai?aeiee caoeno
iai?eeiyoiee.

N1,N1-Aeecai?uai? N2-a?ee- oa N2-aaoa?eeoi?iai?aeeie ? c?o/ieie
nenoaiaie aeey i?iaaaeaiiy aaoa?ioeeee?caoe?e, iaeiae, a e?oa?aoo?? ia
cacia/aii aeiaeiiai i?eeeaaeo neioaco oinoi?iai?nieo aaoa?ioeeee?a,
aeoiaey/e c o?ecai?uaieo oi?iai?aeei?a. Oaeee noai ni?aa, i/aaeaeii, aoa
coiiaeaiee aaaeeiaeinooii?noth nenoai, ui i?noyoue a non?aei?o
iieiaeaiiyo ai?aeeiiaee cai?niee oa ioeeaio?eueio oinoi?io ooieoe?th.

?ic?iaeai? ia i?eeeaae?
N1,N1-aeeiaoee-N2-(1-oai?e-3-iaoee-5-i??acie?e)oi?iai?aeeio 2.4 iaoiaee,
ui aeicaieeee aaanoe eeth/iao a oinoi?i?aai?/i?e o?i?? Cl2P-ooieoe?th a
non?aei? aei oi?iai?aeeiiaiai cai?nieea iieiaeaiiy, a?aee?eaathoue
iiaeeeaino? aeey iiaeeo?eaoe?? ioeeaio?eueii? oinoi?ii? ooieoe?? oa
aeine?aeaeaiiy ?? a aaoa?ioeeee?caoe?yo. Aeey oinoaciniieoe oa ?e?ae?a
oinoi?o aeanoeaa aeniea ioeeaio?euei?noue, naia oiio aiie aoee aea?ai?
iiaeaeueieie a neioac? oinoi?iai?nieo aaoa?ioeeee?/ieo nenoai.

Aioo??oiueiiieaeo?ia aaoa?ioeeee?caoe?y aaaea aei iiaeo
aaoa?ioeeee?/ieo nenoai: i??aciei[4,5-e]-1,3,45-ae?acaoino?i?io 3.17 oa
i??aciei[5,4-b]-1,45-acaoino?i?io 3.19, no?oeoo?a yeeo
i?aeoaa?aeaeo-aaeanue ca aeiiiiiaith 13C, 1H, 31P ssI? iaoiae?a, a
oaeiae ian-niaeo?ineii??.

AENIIAEE

1. N1,N1-Aeeiaoee-N2-aaoa?eeoi?iai?aeeie oinoi?eeththoueny aaeiaai?aeaie
o?eaaeaioiiai oinoi?o a iniiaiiio na?aaeiaeu? a?ey aaoa?ioeeee?/iiai
caeeoeo.

2. 3-Iaoee-1,3-ae?acaaoo-1-?i?eueiee cai?niee ia? neeuei?
aeaeo?iiiaeiii?i? aeanoeaino?, ye? a cia/i?e i??? ni?eythoue
oinoi?eethaaiith nenoai, ui caciathoue aeaeo?io?eueiiai cai?uaiiy ca
aaoa?ia?aiii??aei iaoai?ciii.

3. N1,N1-Aeeiaoee-N2-2-[1,3,4]-o?aae?acie?eoi?iai?aeei ? cia/ii a?eueoa
?aaeoe?eiicaeaoiei noano?aoii a ?aaeoe?? aeaeo?io?eueiiai
oinoi?eethaaiiy, i?ae N1,N1-aeeiaoee-N2-2-o?acie?eoi?iai?aeei, ia
aeeaey/enue ia iayai?noue o ia?oiio aeiaeaoeiaiai
aeaeo?iiiaeoeaioi?-iiai i??eaeeiiaiai aoiia acioo. Oea iaoiiaeaia,
i/aaeaeii, ??cieie iaoai?ciaie aeaeo?io?eueiiai cai?uaiiy: a ia?oiio
aeiaaeeo – ?e?aeiei, a ae?oaiio – aaoa?ia?aiii??aei.

4. Oinoi?eethaaiiy N,N’-aee(aao)a?eeoi?iai?aeei?a ? iiaei iaoiaeii
iaea?aeaiiy 1,4,2,5-ae?acaaeeoinoi?eiai?a.

5. 3-Iaoee-1,3-ae?acaaoo-1-?i?eueiee cai?niee, caaaeyee
aeaeo?iii-aeiii?iei aeanoeainoyi, cieaeo? i?oei?noue N-? ca’yceo a
N-oinoi?e-eueiaaieo N-acie?eoi?iai?aeeiao.

6. Iaci?ii?noue oi?iai?aeeiiai? ooieoe?? i?e aeaeo?io?eueiiio
oinoi?eethaaii? N1,N1-aeeiaoee-N2-acie?eoi?iai?aeei?a, a oaeiae
eaae?noue ?? ia?aoai?aiiy a ai?ii- /e oi?iai?aeio ooieoe?? a oiiaao
eoaeiiai aai eeneiai a?ae?ie?co a?aeiia?aeii, coiiaeththoue
ia?niaeoeai?noue ?? aeei?enoaiiy ye caoenii? a?oie i?e oinoi?eethaaii?
ai?iiiio?aeieo aeine?aeaeaieo aaoa?ioeeee?/ieo niieoe, aea eeane/iee
aoeaoai?aeiee caoeno iai?eeiyoiee.

7. Aioo??oiueiiieaeoey?ia aca?iiae?y ioeeaio?eueii? oinoi?ii? ooieoe??
oa oi?iai?aeeiiaiai cai?nieea, ui ciaoiaeyoueny a non?aei?o iieiaeaiiyo
aaoa?ioeeeeo – iiaee i?aeo?ae a neioac? oinoi?iai?nieo aaoa?ioeeee?/ieo
niieoe. Ia i?eeeaae? oinoaciniieoe oa ?e?ae?a oinoi?o, iio?aeieo
N1,N1-aeeiaoee-N2-5-i??acie?eoi?iai?aeeio, ?aae?ciaaii neioac iiaeo
aaoa?ioeeee?/ieo nenoai: i??aciei[4,5-e]-1,3,45-ae?acaoino?i?io oa
i??aciei[5,4-b]-1,45-acaoino?i?io.

Iniiaiee ci?no aeena?oaoe?? aeeeaaeaii o oaeeo ?iaioao:

1. Oshovsky G.V., Pinchuk A.M., Tolmachev A.A. Amidine function in
constructing novel types of phosphoruscontaining heterocycles //
Mendeleev Communications. – 1999. – V.9. – ?4. – p. 161-162.

2. Oshovsky G.V., Pinchuk A.M, Chernega A.N., Pervak I.I., Tolmachev
A.A. Novel heterocyclizations of N,N’-Diarylform-amidines;
1,4,2,5-diazadiphosphorinanes // Mendeleev Communications. – 1999. –V.9.
– ?1. – p.38–39.

3. Ioianeee A.A., Oieia/aa A.A., TH?/aiei A.A., Ia?eoeia A.N., Iei/oe
A.I. N-Oinoi?eee?iaaiiua N’-2-oeacieeeoi?iaieaeeiu // Eca. AI., Na?.
Oei. – 1999. – 7. – N. 1353–1359.

4. Ioianeee A.A., Oieia/aa A.A., Ia?eoeia A.N., Iei/oe A.I.
Oinoi?eee?iaaiea N,N-aeeiaoee-N’-2-oeaaeeacieeeoi?iaieaeeia // OAN. –
1997. – ?10. – n. 1422–1424.

5. Oieia/aa A.A., Ioianeee A.A., Ia?eoeia A.N., Iei/oe A.I.
Oinoi?eee?iaaiea N,N-aeeiaoee-N’-(2-oeacieee)oi?iaieaeeia – i?inoie
iooue e 5-oinoi?eee?iaaiiui 2-aieiioeacieai // OAN. – 1996. – ?9. – n.
1288–1289.

6. Oshovsky G.V., Pinchuk A.M., Yurchenko A.A. C-Phosphorylated
N,N-dimethyl-N’-hetarylformamidines // Proc. International Conf. on
Phosphorus Chem. XIV. – Cincinnati (USA). – 1998. – P. LF2-7.

7. Ioianeee A.A., Iei/oe A.I., Ia?eoeia A.N. Oi?iaieaeeiu a neioaca
oinoi?niaea?aeaueo aaoa?ioeeeee/aneeo niaaeeiaiee ni naycueth
oinoi?-oaea?iae // O?oaeu Iaaeaeoia?. eiio. ii oeiee e i?eiaiaieth
oinoi?-, na?a- e e?aiieei?aaie/aneeo niaaeeiaiee “Iaoa?ao?aneea
ano?a/e-98”. – Naieo-Iaoa?ao?a (?inney). – 1998. – N. 173.

8. Ioianueeee A.A., I?i/oe I.I., Ia?aae ?.?., Ia?eoeia A.N. ?e?aeia
aeaeo?io?eueia cai?uaiiy a?ey oi?iai?aeeiiaiai aoaeaoeaaiai aoiia //
Oace Oe?a?inueei? eiioa?aioe?? c i?aai?/ii? o?i?? XVIII. –
Aei?i?iiao?ianuee (Oe?a?ia). – 1998. – N. 21.

9. Ioianeee A.A. Aaoa?ioeeeeecaoeee N-oinoi?eee?iaaiiuo
N-aao-a?eeoi?iaieaeeiia // O?oaeu Ana?inneeneie eiioa?aioeee “Oeiey
oinoi?i?aaie/aneeo niaaeeiaiee e ia?niaeoeau aa ?acaeoey ia ii?iaa XXI
aaea”, iinayuaiiie iaiyoe I. E. Eaaa/ieea. – Iineaa (?inney). – 1998. –
N. 44.

10. Ioianueeee A.A. N-Oinoi?eethaaiiy N,N’-ae?a?eeoi?iai?aeei?a // Oace
Oe?a?inueei? eiioa?aioe?? “O?i?y acioiai?nieo aaoa?ioeeee?a”. – Oa?e?a
(Oe?a?ia). – 1997. – N. 163.

AIIIOAOeEss

Ioianeee A. A.

Oinoi?eee?iaaiea N-acieeeoi?iaieaeeiia. – ?oeiienue.

Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oeie/aneeo iaoe ii
niaoeeaeueiinoe 02.00.08 – oeiey yeaiaioii?aaie/aneeo niaaeeiaiee. –
Einoeooo i?aaie/aneie oeiee Iaoeeiiaeueiie Aeaaeaiee Iaoe Oe?aeiu, Eeaa,
1999.

Caueuaaony 5 iao/iuo ?aaio, iinayuaiiuo enneaaeiaaieth oinoi?eee?iaaiey
N-acieeeoi?iaieaeeiia, a oaeaea eco/aieth naienoa oinoi?eee?iaaiiuo
i?iaeoeoia.

A ?aaioa aia?aua iieacaii, /oi N1,N1-aeeiaoee-N2-aaoa?eeoi?iaieaeeiu
oinoi?eee?othony ii aaoa?ioeeeee/aneiio inoaoeo aaeiaaieaeaie
o?aoaaeaioiiai oinoi?a a iniiaiuo n?aaeao. Ia i?eia?a ?yaea
N-acieeeaieaeeiia, i?iecaiaeiuo ie?aciea, oeaciea, 1,3,4-oeaaeeaciea,
1,2,4-o?eaciea ?ac?aaioaiu i?aia?aoeaiua iaoiaeu neioaca
N-oinoi?eee?iaaiiuo aaoa?ioeeeee/aneeo niaaeeiaiee, niaea?aeaueo
naiaiaeiue aieaeeiiaue caianoeoaeue.

Iieacaia e enneaaeiaaia iiiaiooieoeeiiaeueiinoue –N=CH–NMe2 a?oiiu a
?aaeoeee yeaeo?ioeeueiiai oinoi?eee?iaaiey acieia:

a) neeueiua yeaeo?iiiaeiii?iua naienoaa, cia/eoaeueii iaeaa/athuea
aaaaeaiea oinoi?iie ooieoeee e -yeaeo?iii-aioioa?iui aaoa?ioeeeeai;

b) caueoiua naienoaa, aeaeathuea eaaeiaeinooiiuie ?yae
aieiiaaoa?ioeeeeia n ?acee/iuie a?oiie?iaeaie o?ao- e iyoeaaeaioiiai
oinoi?a;

c) niiniaiinoue ?aaae?iaaoue n N-ioeeaioeeaie (ia?aaieie?iaaiea iiae
aeaenoaeai aoi?e/iuo aieiia) aeaeaao eaaeiaeinooiiuie
N-oinoi?eee?iaaiiua aaoa?ioeeeeu n ?acee/iuie aieaeeiiauie
caianoeoaeyie.

I?aaeeiaeai iiaue iiaeoiae e neioaco oinoi?niaea?aeaueo
aaoa?ioeeeee/aneeo niaaeeiaiee, iniiaaiiue ia aioo?eiieaeoey?iii
acaeiiaeaenoaee ioeeaioeeueiie oinoi?iie ooieoeee e oi?iaieaeeiiaiai
caianoeoaey, iaoiaeyuaainy a ninaaeiai iieiaeaiee aaoa?ioeeeea. Ia
i?eia?a eeeaeia e oinoaciaeae?eaeia, i?iecaiaeiuo ie?aciea,
neioace?iaaiu iiaua aaoa?ioeeeee/aneea nenoaiu:
ie?aciei[4,5-e]-1,3,45-aeeacaoinoeiei e
ie?aciei[5,4-b]-1,45-acaoinoeiei.

Enneaaeiaaii oinoi?eee?iaaiea N,N’-aeecaiauaiiuo oi?iaieaeeiia.
Iieacaii, /oi, iacaaeneii io caianoeoaeae, oinoi?iay ooieoeey aaiaeeony
e aoiio acioa e oi?iaieaeeiiaiio aoiio oaea?iaea – yoi
i?aaenoaaeyao iiaue iaoiae neioaca 1,4,2,5-aeeacaaeeoinoi?eiaiia.
Iineaaeiea auee auaeaeaiu a aeaea iaieo eciia?ia (oeen- e o?ain-).

I?aaeeiaeaiiua iiaeoiaeu e ?ac?aaioaiiua iaoiaeu eiatho oai?aoe/aneia e
i?aia?aoeaiia cia/aiea.

Eeth/aaua neiaa: N-acieeeoi?iaieaeeiu, ie?acie, oeacie,
1,3,4-oeaaeeacie, 1,2,4-o?eacie, oinoi?eee?iaaiea, aaoa?ioeeeeecaoeee,
caueoiay a?oiia, 1,4,2,5-aeeacaaeeoinoi?eiaiu.

AIIOAOe?ss

Ioianueeee A. A.

Oinoi?eethaaiiy N-acie?eoi?iai?aeei?a. – ?oeiien.

Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo
iaoe ca niaoe?aeuei?noth 02.00.08 – o?i?y aeaiaioii?aai?/ieo niieoe. –
?inoeooo i?aai?/ii? o?i?? Iaoe?iiaeueii? Aeaaeai?? Iaoe Oe?a?ie, Ee?a,
1999.

Caoeua?oueny 5 iaoeiaeo ?ia?o, i?enay/aieo aeine?aeaeaiith
oinoi?eethaaiiy N-acie?eoi?iai?aeei?a, a oaeiae aea/aiith aeanoeainoae
oinoi?eeueiaaieo i?iaeoeo?a.

A ?iaio? aia?oa iieacaii, ui N1,N1-aeeiaoee-N2-aaoa?ee-oi?iai?aeeie
oinoi?eeththoueny a?ey aaoa?ioeeee?/iiio caeeoeo aaeiaai?aeaie
o?eaaeaioiiai oinoi?o a iniiaiiio na?aaeiaeu?. Ia i?eeeaae? ?yaeo
N-acie?eoi?iai?aeei?a, iio?aeieo i??acieo, o?acieo, 1,3,4-o?aae?acieo,
1,2,4-o?eacieo, ?ic?iaeai? i?aia?aoeai? iaoiaee neioaco
N-oinoi?eeueiaaieo aaoa?ioeeee?/ieo niieoe, ui i?noyoue iacai?uaio
ai?aeeiiao ooieoe?th.

Iieacaia aaaaoiooieoe?iiaeuei?noue –N=CH–NMe2 a?oie a ?aaeoe??
aeaeo?io?eueiiai oinoi?eethaaiiy acie?a:

a) neeuei? aeaeo?iiiaeiii?i? aeanoeaino?, ui cia/ii iieaaoo? aaaaeaiiy
oinoi?ii? ooieoe?? aei -aeaeo?iiiaioioa?ieo aaoa?ioeeee?a;

b) caoeni? aeanoeaino?, ui ?iaeyoue eaaeiaeinooiieie ?yae
ai?iiaaoa?ioeeee?a c ??cieie oa?oioaaiiyie o?e- oa i’yoeaaeaioiiai
oinoi?o;

c) caeaoi?noue ?aaaoaaoe c N-ioeeaio?eaie (ia?aai?ioaaiiy i?ae ae??th
aoi?eiieo ai?i?a) ?iaeoue eaaeiaeinooiieie N-oinoi?eeueiaai?
aaoa?ioeeeee c ??cieie ai?aeeiiaeie cai?nieeaie.

Cai?iiiiiaaii iiaee i?aeo?ae aei neioaco oinoi?iai?nieo aaoa?ioeeee?/ieo
niieoe, ui aaco?oueny ia aioo??oiueiiieaeoey?i?e aca?iiae??
ioeeaio?eueii? oinoi?ii? ooieoe?? oa oi?iai?aeeiiaiai cai?nieea, ye?
ciaoiaeyoueny a non?aei?o iieiaeaiiyo aaoa?ioeeeeo. Ia i?eeeaae? ?e?ae?a
oa oinoacia?ae?eae?a, iio?aeieo i??acieo, neioaciaai? iia?
aaoa?ioeeee?/i? nenoaie: i??aciei[4,5-e]-1,3,45-ae?acaoino?iei e
i??aciei[5,4-b]-1,45-acaoino?iei.

Aeine?aeaeaii oinoi?eethaaiiy N,N’-aeecai?uaieo oi?iai?aeei?a. Iieacaii,
ui, iacaeaaeii a?ae cai?niee?a, oinoi?ia ooieoe?y aaiaeeoueny aei aoiia
acioo oa oi?iai?aeeiiaiai aoaeaoeaaiai aoiia – oea yaey? niaith iiaee
iaoiae neioaco 1,4,2,5-ae?acaaeeoin-oi?eiai?a. Inoaii? aoee aeae?eai? o
aeaeyae? iaio ?ciia??a (oeen- oa o?ain-).

Cai?iiiiiaai? i?aeoiaee oa ?ic?iaeai? iaoiaee iathoue oai?aoe/ia oa
i?aeoe/ia cia/aiiy.

Eeth/ia? neiaa: N-acie?eoi?iai?aeeie, i??acie, o?acie,
1,3,4-o?aae?acie, 1,2,4-o?eacie, oinoi?eethaaiiy, aaoa?ioeeee?caoe??,
caoenia a?oia, 1,4,2,5-ae?acaaeeoinoi?eiaie.

ANNOTATION

Gennady V. Oshovsky

Phosphorylation of N-azolylformamidines. – Manuscript.

Dissertation for receiving the Candidate of Sciences (Ph. D.)
scientific degree in chemistry by speciality 02.00.08 – the chemistry of
elementoorganic compounds. – Institute of organic chemistry of the
National Academy of Sciences of Ukraine, Kyiv, 1999.

Five scientific works devoted to investigating the phosphorylation of
N-azolylformamidines, as well as to the research of the phosphorylated
products’ properties are defended.

It was first showed in this work, that
N1,N1-dimethyl-N2-hetarylformamidines undergo C-phosphorylation at the
heterocyclic moiety by trivalent phosphorus halides in the basic medium.
Synthetic approaches to C-phosphorylated heterocyclic compounds
containing unsubstituted amidine function have been elaborated on the
base of model N-azolylformamidines being the derivatives of pyrazole,
thiazole, 1,3,4-thiadiazole and 1,2,4-triazole.

Polyfunctionality of –N=CH–NMe2 in electrophilic phosphorylation
reaction has been found and researched. It is featured by such the
items:

a) strong electronodonating properties considerably facilitating the
introduction of phosphorus function to electronoamphoteric heterocycles;

b) protecting properties, what allow ease access to a range of
aminoheterocycles containing different functions with ter- and
pentavalent phosphorus;

c) transamination under action of the secondary amines making
C-phosphorylated heterocycles with different amidine functions to be
accessible.

It was proposed novel approach to the synthesis of phosphoruscontaining
heterocyclic compounds based on intermolecular interaction of
nucleophilic phosphorus function and neighbor amidine substituent. New
heterocyclic systems, pyrazolo[4,5-e]-1,3,45-diazaphosphinine and
pyrazolo[5,4-b]-1,3,45-azaphosphinine, have been prepared proceeding
from pyrazole ylides and phosphazohydrides.

The phosphorylation of N,N’-disubstituted formamidines has been
investigated. The phosphorus function was showed to introduce at
nitrogen atom and to formamidine carbon atom regardless of the
substituent at the imine nitrogen atom. It is new approach to
1,4,2,5-diazadiphosphorinanes, which were prepared as two isomers (cis-
and trans-).

The proposed approaches and elaborated methods are of theoretical and
synthetic importance.

Keywords: N-azolylformamidines, pyrazole, thiazole, 1,3,4-thiadiazole,
1,2,4-triazole, phosphorylation, heterocyclization, protecting group,
1,4,2,5-diazadiphosphorinanes.

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