Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
1,3-Dipolar Cycloaddition of Ylides Generated from Diazines and Dichlorocarbene. / Khlebnikov, A. F.; Kostik, E. I.; Kopf, J.; Aleksandrov, E. V.; Kostikov, R. R.
в: Russian Journal of Organic Chemistry, Том 34, № 5, 05.1998, стр. 712-724.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - 1,3-Dipolar Cycloaddition of Ylides Generated from Diazines and Dichlorocarbene
AU - Khlebnikov, A. F.
AU - Kostik, E. I.
AU - Kopf, J.
AU - Aleksandrov, E. V.
AU - Kostikov, R. R.
N1 - Copyright: Copyright 2004 Elsevier Science B.V., Amsterdam. All rights reserved.
PY - 1998/5
Y1 - 1998/5
N2 - Reaction of dichlorocarbene with diazines in the presence of dimethyl maleate and dimethyl acetylenedicaroxylate involves intermediate formation of ylides, namely cycloimmoniodichloromethanides, followed by 1,3-dipolar cycloaddition of the latter to dipolarophiles. This carbene-ylide sequence was used to synthesize chloro-substituted pyrrolo[1,2-6]pyridazines, pyrrolo[1,2-c]- and pyrrolo[1,2-a]pyrimidines, pyrrolo[1,2-a]phthalazine, pyrrolo[1,2-a]-, pyrrolo[1,2-c]-, and pyrrolo[2,1-b]quinazolines, pyrrolo[1,2-a]-quinoxalines, and pyrrolo[1,2-a]naphthiridines. The cycloaddition is stereo- and regioselective, which suggests a concerted reaction mechanism. The regioselectivity of the cycloaddition is correctly predicted in terms of the PMO theory on the basis of MNDO electronic parameters of halogenated cycloimmonium ylides.
AB - Reaction of dichlorocarbene with diazines in the presence of dimethyl maleate and dimethyl acetylenedicaroxylate involves intermediate formation of ylides, namely cycloimmoniodichloromethanides, followed by 1,3-dipolar cycloaddition of the latter to dipolarophiles. This carbene-ylide sequence was used to synthesize chloro-substituted pyrrolo[1,2-6]pyridazines, pyrrolo[1,2-c]- and pyrrolo[1,2-a]pyrimidines, pyrrolo[1,2-a]phthalazine, pyrrolo[1,2-a]-, pyrrolo[1,2-c]-, and pyrrolo[2,1-b]quinazolines, pyrrolo[1,2-a]-quinoxalines, and pyrrolo[1,2-a]naphthiridines. The cycloaddition is stereo- and regioselective, which suggests a concerted reaction mechanism. The regioselectivity of the cycloaddition is correctly predicted in terms of the PMO theory on the basis of MNDO electronic parameters of halogenated cycloimmonium ylides.
UR - http://www.scopus.com/inward/record.url?scp=0032257555&partnerID=8YFLogxK
M3 - Article
VL - 34
SP - 712
EP - 724
JO - Russian Journal of Organic Chemistry
JF - Russian Journal of Organic Chemistry
SN - 1070-4280
IS - 5
ER -
ID: 5057223