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Regioselectivity of nitrilimines 1,3-dipolar cycloaddition: Novel synthesis of spiro[4,4]nona-2,8-dien-6-one derivatives

✍ Scribed by Omar A. Miqdad; Nada M. Abunada; Hamdi M. Hassaneen

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
197 KB
Volume
22
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Regioselective 1,3‐dipolar cycloaddition of nitrilimines (generated in situ from dehydrohalogenation of the corresponding hydrazonoyl halides by the action of triethylamine) with 4‐arylidene‐1‐aryl‐2‐phenyl‐1__H__‐imidazol‐5(4__H__)‐one 3 afforded the corresponding spiro[4,4]nona‐2,8‐dien‐6‐one 4. The reaction was carried out in dry benzene under reflux temperature. Refluxing in acetic acid, 4a was converted to its respective N‐phenylpyrazole‐5‐carboxamide 8. The structures of prepared compounds were established by elemental analyses and spectral data (IR, MS, ^1^H, and ^13^C NMR). © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:131–136, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20666

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