Synthesis of some new Indeno[1,2-e]pyrazolo[5,1-c]-1,2,4-triazin-6-one and Indeno[2,1-c]pyridazine-4-carbonitrile Derivatives

Hamdi M. Hassaneen, Nada M. Abunada, Huwaida M. Hassaneen
2010 Natural Science  
Diazonium chlorides of 5-amino-3-methypyrazole 1a and 5-amino-4-phenylpyrazole 1b coupled with 1,3-indanedione 2 and led to the formation of acyclic hydrazone 3a and a cyclic product indenopyrazolotriazine 4b respectively. Cyclization of the hydrazone 3a by boiling in acetic acid afforded the corresponding 4a. The hydrazone 3a reacted with malononitrile in boiling ethanol in the presence of piperidine and gave indeno[2,1-c]pyridazine-4-carbonitrile derivatives 5a,b. Also, coupling of 6 with
more » ... pling of 6 with aryl diazonium chlorides gave the corresponding indenopyridazine derivatives 8a-e. Acetylation, benzoylation and hydrolysis of compound 8a afforded the corresponding substitution products 10-12, respectively. The structures of the newly synthesized compounds were established on the basis of chemical and spectral evidences. Scheme 1. synthesis of hydrazono-1,3-indanedione 3a, indeno[1,2-e]pyrazolo[5,1-c]triazin-6-one 4a,b and indeno[2,1-c]pyridazines 5a,b. Openly accessible at H. M. Hassaneen et al. 135 1353 Scheme 2. Synthesis of iminoindeno[2,1-c]pyridazines 8 and its N-acetyl, N-benzoyl and oxo-derivatives 9-11. H. M. Hassaneen et al.
doi:10.4236/ns.2010.212164 fatcat:qoxrlbmxsrextpssru2cdazwpe