THE MANNICH REACTION IN THE SYNTHESIS OF N,S-CONTAINING HETEROCYCLES. 3. UNEXPECTED DIRECTION OF THE AMINOMETHYLATION REACTION OF N-METHYLMORPHOLINIUM 1-AMINO-2,4-DICYANO-4-ETHOXYCARBONYL-1,3-BUTADIENETHIOLATE. ONE STAGE CASCADE SYNTHESIS OF NEW DERIVATIVES OF PYRIDO[1,2-<i>a</i>][1,3,5]TRIAZINE

Authors

  • В. В. Доценко ChemEx Laboratory, East-Ukrainian Vladimir Dal National University, Lugansk 91034
  • С. Г. Кривоколыско ChemEx Laboratory, East-Ukrainian Vladimir Dal National University, Lugansk 91034
  • Э. Б. Русанов Institute of Organic Chemistry, National Academy of Sciences of Ukraine; Kiev 02094
  • А. В. Гутов Institute of Organic Chemistry, National Academy of Sciences of Ukraine; Kiev 02094
  • В. П. Литвинов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913

DOI:

https://doi.org/10.1007/7454

Keywords:

N-methylmorpholinium 1-amino-2, 4-dicyano-4-ethoxycarbonyl-1, 3-butadienethiolate, pyrido[1, 2-a][1, 3, 5]triazines, cascade heterocyclization, Mannich reaction, X-ray structural analysis

Abstract

The interaction of N-methylmorpholinium 1-amino-2,4-dicyano-4-ethoxycarbonyl-1,3-butadienethiolate with primary amines and formaldehyde leads to the formation of ethyl esters of 7-cyano-6-thioxo-1,3,4,6-2H-pyrido[1,2-a][1,3,5]triazine-9-carboxylic acid in place of the expected derivatives of pyrido[2,1-b][1,3,5]thiadiazine. The structure of  the ethyl ester of 7-cyano-3-phenyl-6-thioxo-1,3,4,6-2H-pyrido[1,2-a][1,3,5]triazine-9-carboxylic acid was demonstrated by X-ray structural analysis.

How to Cite
Dotsenko, V. V.; Krivokolysko, S. G.; Rusanov, E. B.; Gutov, A. V.; Litvinov, V. P.  Chem. Heterocycl. Compd. 2007, 43, 906. [Khim. Geterotsikl. Soedin. 2007, 1075.]

For this article in the English edition see DOI 10.1007/s10593-007-0143-5

 

Published

2023-02-15

Issue

No. 7 (2007)

Section

Original Papers