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: Scientific Explanation

In an EtOH/TEA solution at room temperature, ethyl 2-(benzo[d]thazol-2-yl)acetate (3) was combined with various arylidinemalononitrile derivatives (4a-c) to produce the compounds shown. The ethyl iminothiazolopyridine-4-carboxylate (6) was produced by treating 3 with 2- (ethoxymethylene)-malononitrile (4f) under the same reaction conditions. On the basis of a reaction of 3 with various cyanoacrylate derivatives (7a,b) in MeOH/TEA at room temperature, ethyl (amino(methoxy)methyl)-3-(substitutedphenyl)-1-oxo-1H-benzo[4,5]thiazole[3,2-a]pyridine-4- carboxylate (8a,b) was produced. Under the same reaction conditions, the diethyl thiazolo[3,2-a]pyridine-4-carboxylate derivative (8c) was produced. The amino-imino derivative (10) was also completely produced and used to make new pyrido[3,2-e][1,2,4]triaziolo[1,5-c]pyrimidine-5-carboxylate derivatives (12). The structures of all of the newly synthesised compounds were verified using elemental analysis and spectroscopic data. When 10a was treated with electrophilic reagents, the triazolo[1,5-c]pyrimidine-5-carboxylate derivatives (12a-c) were produced.

Author (S) Details

Hany M. Mohamed
Chemistry Department, Faculty of Medicine, Jazan University, Jazan, Saudi Arabia and Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt.

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