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Microwaves in organic synthesis: Synthesis of pyridazinones, phthalazinones and pyridopyridazinones from 2-oxo-arylhydrazones under microwave irradiation

✍ Scribed by Balkis Al-Saleh; Morsy Ahmed El-Apasery; Noha M. Hilmy; Mohamed H. Elnagdi

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
375 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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The phenylhydrazones 1a‐d condensed with ethyl cyanoacetate to yield pyridazinones 2a‐d that reacted with sulphur in presence of piperidine to yield the aminothienopyridazineones 3a,b that reacted with electron poor olefins and acetylenes to yield phthalazines 10‐12. The condensed aminothiophenes 3a,b reacted with dimethylformamide dimethylacetal to yield amidines 13a,b. Compounds 2a,b condensed with dimethylformamide dimethylacetal to yield the trans enamines 16a,b that cyclized readily into the pyridopyridazinones 17a,b on treatment with ammonium acetate in presence of acetic acid. Compounds 2a‐d reacted also with benzylidenemalononitrile to yield the phthalazinones 21a‐d. The reactions were conducted both by microwave heating and conventional heating. Better yields in much shorter reaction times were achieved by microwave heating.

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