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Paper | Regular issue | Vol 75, No. 9, 2008, pp.2201-2211
Published online, 21st April, 2008
DOI: 10.3987/COM-08-11373
Studies on Enamines and Azaenamines: 2-Oxoarylhydrazonals as C-1 Nucleophiles

Saleh M. Al-Mousawi,* Moustafa Sherief Moustafa, and Mohamed Hilmy Elnagdi

*Department of chemistry, Faculty of Science; University of Kuwait: Safat; 13060: Kuwait


2-Oxoarylhydrazonals 1a,b react with aldehydes; piperidine; morpholine and benzotriazole to yield the corresponding Mannich bases 2a,f, and 4. Formaldehyde reacts with 1a,b to yield the hydroxymethylarylhyrazons 5a,b together with bisarylhydrazones 6. The hydroxymethyl derivatives 5a are converted to arylhydrazonal 7 upon oxidation in refluxing nitrobenzene. The reaction of aldehydes and malononitrile with 1a,b in ethanolic solution in presence of chitozan as heterogeneous catalyst afforded 6-amino-1,4-dihydropyridazins 14a,b.