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3H-Azepines by Intramolecular Condensation Reaction of 1,6-Diamino-1,3,5-hexatrienes

✍ Scribed by Kowalski, Dorothee ;Erker, Gerhard ;Kotila, Sirpa

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
381 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

2,7‐Disubstituted 3__H__‐azepines (2a–d) are obtained by acidcatalyzed thermolytic deamination of 1,6‐disubstituted 1,6‐diamino‐1,3,5‐hexatrienes 1a–d in moderate yields. The reaction probably involves reversible conjugated enamine ⇌ imine tautomerization indicated by the formation of the respective five‐membered ring competition products 3. Compounds 2a and 3b were characterized by X‐ray diffraction.

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