✦ LIBER ✦
Functionalized enamines XXIX. Solvolytic transformations of 2-methylisoquinolin-1-one dichlorocarbene adduct. Synthesis of benzazepinones
✍ Scribed by H. P. Soetens; U. K. Pandit
- Book ID
- 104588251
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 387 KB
- Volume
- 99
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
Dichlorocarbene, generated from base‐catalysed decomposition of chloroform, adds to the double bond of 2‐methylisoquinolin‐1‐one (1), to give the 1:1 adduct (2). The latter adduct reacts with water to give E‐3‐(formylmethylene)‐2‐methylisoindolinone (3a). Refluxing of 2 in alcohols yields alkoxybenzazepin‐1‐ones. Upon heating (of 2) in dimethoxyethane and subsequent reduction with lithium borohydride, 4‐chloro‐2‐methyl‐1H‐2,3‐dihydro‐2‐benzazepinone (10) was obtained as the main product. Mechanisms for the formation of these products are discussed.