A Convenient Synthesis of Ethyl 1-Amino-3-(Substituted Phenyl)-2-Cyano-3H-Benzo[4,5]Thiazolo-[3,2-a]Pyridine-4-Carboxylate Derivatives and Some of their Reactions

Hany M. Mohamed^{1, 2,}

¹Chemistry Department, Faculty of Medicine, Jazan University, Jazan, Saudi Arabia

²Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

Cite this paper:
Hany M. Mohamed. A Convenient Synthesis of Ethyl 1-Amino-3-(Substituted Phenyl)-2-Cyano-3H-Benzo[4,5]Thiazolo-[3,2-a]Pyridine-4-Carboxylate Derivatives and Some of their Reactions. World Journal of Organic Chemistry. 2014; 2(1):1-8. doi: 10.12691/wjoc-2-1-1

Abstract

The titled compounds were prepared by interaction of ethyl 2-(benzo[d]thazol-2-yl)acetate (3) with different arylidinemalononitrile derivatives (4a-c) in EtOH/TEA solution at room temperature. When 3 was treated with 2-(ethoxymethylene)-malononitrile (4f) under same reaction conditions, the ethyl iminothiazolopyridine-4-carboxylate (6) was obtained. Ethyl (amino(methoxy)methyl)-3-(substitutedphenyl)-1-oxo-1H-benzo[4,5]thiazole[3,2-a]pyridine-4-carboxylate (8a,b) was obtained from reaction of 3 with different cyanoacrylate derivatives (7a,b) in MeOH/TEA at room temperature, while the diethyl thiazolo[3,2-a]pyridine-4-carboxylate derivative (8c) was obtained under same reaction conditions. The amino-imino derivative (10) was also prepared and used to synthesis new pyrido[3,2-e][1,2,4]triaziolo[1,5-c]pyrimidine-5-carboxylate derivatives (12). The structures of all the newly synthesized compounds were confirmed based on their elemental analysis and spectroscopic data.

Keywords:
ethyl 2-(benzo[d]thazol-2-yl)acetate arylidinemalononitrile pyridine-4-carboxylate triaziolo[15-c]pyrimidine-5-carboxylate

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