HETEROCYCLIZATION OF FUNCTIONALIZED HETEROCUMULENES WITH C,N- AND C,O-BINUCLEOPHILES. 1. CYCLOCONDENSATION OF 1-CHLOROALKYLHETEROCUMULENES AND N-(1-CHLOROALKYLIDENE)URETHANES WITH 2-CYANOMETHYLPYRIDINE

Authors

  • М. В. Вовк Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • П. С. Лебедь Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • А. Н. Чернега Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • В. В. Пироженко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • В. И. Бойко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • И. Ф. Цымбал Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094

Keywords:

1H-pyrido[1,2-c]pyrimidines, 1-chloroalkyl isocyanates, 1-chloroalkylcarbodiimides, N-(1-chloroalkylidene)urethanes, 2-cyanomethylpyridine, cyclocondensation

Abstract

The interaction of 1-chloroalkyl isocyanates, 1-chloroalkylcarbodiimides, 1,1-dichloroalkyl isocyanates, and N-(1-chloroethylidene)-O-methylurethanes with 2-cyanomethylpyridine has been investigated. An effect of organic base has been detected on the regioselectivity of the cyclocondensation of 1-chloroalkyl isocyanates, which leads to 2,3-dihydro-1H-pyrido[1,2-c]pyrimidin-1-one or the isomeric 2,3-dihydro-1H-pyrido[1,2-c]pyrimidin-3-one. Irrespective of the cyclization conditions 1-chloroalkylcarbodiimides react with the formation of 1-imino-2,3-dihydro-1H-pyrido-[1,2-c]pyrimidines. One type of product, a 1H-pyrido[1,2-c]pyrimidin-1-one, was also isolated from 1,1-dichloroalkyl isocyanates and N-(1-chloroalkylidene)urethanes.

How to Cite
Vovk, M. V.; Lebed, P. S.; Chernega, A. N.; Pirozhenko, V. V.; Boiko, V. I.; Tsymbal, I. F. Chem. Heterocycl. Compd. 2004, 40, 47. [Khim. Geterotsikl. Soedin. 2004, 52.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000023767.14562.04

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Published

2004-01-25

Issue

No. 1 (2004)

Section

Original Papers