Synthesis and biological effects of new derivatives of azines incorporating coumarin

Abstract

New synthetic routes for triazolopyridine, pyridopyrimidine, pyridotriazine, imidazopyridine and pyridazine derivatives incorporating a coumarin moiety with interesting biological activities are reported. Reactions of the 2-oxo-4-(2-dimethylaminoethenyl)-2H-chromene-3-carbonitrile (4) and 2-amino-4-(2-dimethylaminoethenyl)quinoline-3-carbonitrile (5) with benzotriazol-1-yl-acetic acid hydrazide (6) affords the substituted [1,2,4]triazolo [1,5-a]pyrido [3,4-c]coumarines 9 and quinoline 12, respectively. Treatment of 4 with 2-amino-pyridine, glycine, urea, 3-aminocrotononitrile or cyanothioacetamide affords 14-18, respectively. Treatment of 3-amino-3,4-dihydro-4-imino-chromeno[3,4-c]pyridin-5-one (10) with α-chloroacetylacetone affords pyridotriazine derivative 21. Compound 4 was also coupled with benzenediazonium chloride to afford 2-oxo-4-[2-oxo-1-(phenyl-hydrazono)-ethyl]-2H-chromene-3-carbonitrile 25. Treatment of the latter product with malononitrile afforded the 1-phenyl-3-(3'-Cyano-2'-oxo-coumarin-4'-yl)-6-oxopyridazine-5-carbonitrile (27). The structures of the newly synthesized compounds have been established on the basis of analytical and spectral data. The recent literature is enriched with progressive finding about the synthesis and pharmacological results of fused heterocycles. In conjunction with previous interest in the syntheses of polyfunctionally substituted heterocycles with potential biological activites [1][2][3][4][5]. It was interesting to study the behaviour of system A towards a variety of chemical reagents, as a new synthetic route to heterocyclic nitrogen containing compounds, such as triazolopyridine, pyridopyrimidine, pyridotriazine, imidazopyridine, pyridine and pyridazine derivatives incorporating a coumarin moiety. The importance of the above compounds is due to their diverse pharmaceutical activities [6][7][8][9][10][11][12][13] and as thermal-transfer printing dye [14].

Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis

“…Enamine (147) was also coupled with benzenediazonium chloride to afford 2-oxo-4-[2-oxo-1-(phenylhydrazono)-ethyl]-2H-chromene-3-carbonitrile (150). Treatment of (147) with cyanothioacetamide, 3-aminocrotononitrile, urea, glycine, and 2-aminopyridine affords fused heterocyclic compounds (151)(152)(153)(154)(155), respectively, as shown in Scheme 23 [104][105][106].…”

An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity

“…The various biological activities of tetrahydropyran [29][30][31][32], thiazole [33][34][35][36], benzthiazole [37][38][39] and benzimidazole derivatives [40,41] and other hetertocyclic compounds [42,43] prompted us to study the antimicrobial activities of our newly synthesized products. The in vitro antibacterial activities of compounds 9 and 10a-10f were evaluated against Gram positive and Gram negative bacteria (S. aureus, B. subtilis, E. coli and B. cereus) and fungus (Candida albicans) are reported in Table 5.…”

A facile and efficient synthesis of bisazine derivatives

“…In last few years we were involved in a program aimed at designing simple and efficient approaches to polyfunctionally substituted heterocycles utilizing inexpensive, readily obtainable starting materials. During this phase of our research syntheses of azines were developed [12][13][14][15][16][17][18]. We reported here on the synthesis of pyridines and pyrimidines using phenylenediamine as starting material.…”