COMPETITIVE FORMATION OF CONDENSED AZINES AND DIHYDROPYRIDINES IN THE REACTION OF ETHYL 3,3-DIAMINOACRYLATE WITH <i>o</i>-HALO CARBALDEHYDES

Authors

  • И. И. Елисеев (мл.) St. Petersburg State University, St. Petersburg 198504
  • Д. В. Дарьин St. Petersburg State University, St. Petersburg 198504
  • С. И. Селиванов St. Petersburg State University, St. Petersburg 198504
  • П. С. Лобанов St. Petersburg State University, St. Petersburg 198504
  • А. А. Потехин St. Petersburg State University, St. Petersburg 198504

DOI:

https://doi.org/10.1007/7023

Keywords:

benzonaphthyridine, dihydropyridine, ethyl 3, 3-diaminoacrylate, Hantzsch reaction, cyclocondensation

Abstract

The reaction of ethyl 3,3-diaminoacrylate with quinoline-3-carbaldehydes and 3-nitrobenzaldehydes to give a dihydropyridine and condensed azine has been studied with respect to the number and reactivity of the halogen atoms in an ortho position to the formyl groups. For the series of quinoline-3-carbaldehydes it was found that the reaction course is determined by the number of chlorine atoms. 2- and 4-Chloroquinoline-3-carbaldehydes give dihydropyridines and a benzo[c][2,7-]naphthyridine is formed in the reaction with 2,4-dichloroquinoline-3-carbaldehyde. The main products in the case of nitrobenzaldehydes are dihydropyridines which points the deciding influence of the low electrophilicity of aromatic ring.

How to Cite
Eliseev, Jr., I. I.; Dar'in, D. V.; Selivanov, S. I.; Lobanov, P. S.;  Potekhin, A. A.  Chem. Heterocycl. Compd. 2008, 44, 442. [Khim. Geterotsikl. Soedin. 2008, 567.]

For this article in the English edition see DOI 10.1007/s10593-008-0061-1


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Published

2022-09-01

Issue

No. 4 (2008)

Section

Original Papers