NOVEL SYNTHESIS OF 4-(PYRAZOL-5'-YLAZO) ISOQUINOLINE,4-PYRAZOL-5'-YLAZO) FURO [3,4-c]-PYRlDINE,4-(PYRAZOL-5'-YLAZO) PYRROLO [3,4-c] PYRIDINE AND 5-(PYRAZOL-5'-YLAZO) PYRIDO [3,4-d] PYRIDAZINE DERIVATIVES

摘要

Pyrazol-5-ylazopentan-2,4-dione derivative A was condensed with acetonitrile derivatives to give 5-(pyrazol-5'-ylazo) pyridin-2-one derivatives 1a-c.Compounds 1a-c reacted with benzaldehyde to give benzylidene derivatives 2a-c.2a-c reacted with malononitrile to yield 4-(pyrazol-5'-ylazo) isoquinoline derivatives 3a-c.Compound 3a-c could be obtained through reaction of 1a-c with a-cyanocinnamonitrile 4.Also,compound 1a-c reacted with alpha-benzoylcinnamonitrile (5) and ethyl alpha-cyanocinnamate (6) to give 4-(pyrazol-5'-ylazo) isoquinoline derivative 7a-c,8a-c respectively.Bromination of compound 1a-b yielded bromo derivative 9a,b which reacted with phenylhydrazine,ethylamine and sodium hydroxide and potassium cyanide to afford the corresponding products 10a-b-13a-b respectively 13a,b compound could be reacted with p-chlorobenzenediazonium chloride and p-chlorobenzaldehyde to yield the corresponding products 14a,b and 15a,b respectively.Structures of the products were established on the basis of the spectral data and elemental analyses.