1. Utility of 1‐Chloro‐3,4‐dihydronaphthalene‐2‐carboxaldehyde in the Synthesis of Novel Heterocycles with Pharmaceutical Interest.
- Author
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Bondock, Samir, Khalifa, Wesam, and Fadda, AhmedA.
- Subjects
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QUINAZOLINE , *CONDENSATION products (Chemistry) , *SCHIFF bases , *DISINFECTION & disinfectants , *ORGANOSULFUR compounds , *HIPPURIC acid , *AROMATIC amines , *PYRAZOLONES - Abstract
Ethyl a-cyano-ß-(1-chloro-3,4-dihydronaphthalene-2-yl) acrylate (2) was prepared by the Knoevenagel condensation of 1 with ethyl cyanoacetate. Compound 2 was used as the key intermediate to prepare Schiff bases (3a, b), benzo[ c ]acridine (4), naphthyl thiopyrimidine (5), and pyrazolo[2,3- a ]-benzo[ h ]quinazoline (6) derivatives through its reaction with hydrazines, p-ansidine, thiourea, and 3,5-diamino-4-phenylazopyrazole, respectively. Base-catalyzed cyclocondensation of 1 with hippuric acid gives oxazolone derivative (7). Reaction of compound 7 with aniline gave imidazolone derivative (9). Treatment of compound 1 with different types of diaminopyrazoles gave 6,7-dihydro-pyrazolo[2,3- a ]-benzo[ h ]quinazoline (10–13) derivatives. The multicomponent reaction of compound 1 with pyrazolone and malononitrile in the presence of ammonium acetate furnished pyrazolo[3,4- b ]-benzo[ h ]quinoline (14) while in the presence of piperidine afforded benzo[ h ]chromeno[2,3- c ]pyrazole derivative 15. [ABSTRACT FROM AUTHOR]
- Published
- 2006
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