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Communication | Regular issue | Vol 12, No. 2, 1979, pp.231-237
Published online, 1st January, 1970
DOI: 10.3987/R-1979-02-0231
■ Cycloaddition Reactions of Diphenylketene with 1-Aza-1,3-diene and Conjugated Sulfilimines

Masanori Sakamoto,* Kyoko Miyazawa, Keiko Kuwabara, and Yoshio Tomimatsu

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

The cycloaddition reactions of diphenylketene (I) with several azadienes have been examined. 2-Styrylthiazoline (IIa-c) and I generally underwent a 4+2 cycloaddition to give thiazolo[3,2-a]pyridines (IIIa-c). On the other hand, reaction of I with 2-styrylquinoline and 2-styrylpyridine gave rise to a 2+2+2 cycloaddition products (Va, b), respectively. Similar reaction of I with 6-styrylphenanthridine gave pyrido[1,2-f]phenanthridine (VII) and a lactone (Vc).
The orientation of the addition products of I with sulfilimines (VIII, XI, XII) which we reported in our previous paper was the error and the reverse.