Intramolecular 1, 3-dipolar cycloadditions and intramolecular ene reactions of 2-(alkenyloxy) benzaldehyde arylhydrazones.

…, Y Hayashi, Y Kitora, K Teramura

Index: Shimizu, Tomio; Hayashi, Yoshiyuki; Kitora, Yoshitaka; Teramura, Kazuhiro Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 8 p. 2450 - 2455

Full Text: HTML

Citation Number: 32

Abstract

2-(3-Aryl-2-propenyloxy) benzaldehyde (or 1-naphthaldehyde) arylhydrazones undergo an intramolecular cycloaddition reaction via their 1, 3-dipolar tautomers, azomethine imines, to the alkenyl group. Initial cycloadducts were converted to dehydrogenated compounds under the reaction conditions. On the other hand, introduction of cyano or ethoxycarbonyl groups instead of the aryl group into 3-position of the ortho propenyloxy group gave 3- ...