SYNTHESIS OF SOME NOVEL BIS(PYRAZOLE), BIS(PYRIDINE) AND BIS(PYRAZOLO[5,1-c]-1,2,4-TRIAZINE DERIVATIVES

摘要

Treatment of N,N'-(ethane-1,2-diyl)bis(cyanoacetamide) (1) with hydrazonoyl chlorides 2a,b afforded bis(aminopyrazoles) 5a,b. Heating of compound 1 with arylmethylenepropanedinitrile 9a-c afforded bis(pyridine) derivatives 13a-c. Also, compound 1 coupled smoothly with the arenediazonium salt generated from 3-chloroaniline or 5-amino-4-methyl-3-phenylpyrazole (16) to afford the corresponding hydrazones 15 or bis(pyrazolo[5,1-c]-l,2,4-triazine-3-carboxamide) 19. Refluxing of compound 1 with N,N-dimethylformarnide dimethyl acetal (DMF-DMA) in xylene afforded bis(2-cyano-3-(dimethylamino)-acrylamide) (20) which reacted with hydrazine hydrate to afford the novel bis(cyanoopyrazole) 23.