The Synthesis of Annulated Azepin??3??one Derivatives from 1, 3, 4??Pentatrienyl Nitrones by a Heterocyclization− Rearrangement Sequence

K Knobloch, M Keller…

Index: Knobloch, Karin; Keller, Manfred; Eberbach, Wolfgang European Journal of Organic Chemistry, 2001 , # 17 p. 3313 - 3332

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Citation Number: 19

Abstract

Abstract Treatment of various o-propargylaryl nitrones of type 6 with potassium hydroxide or sodium methoxide in methanol at room temperature provides 1, 2-dihydro [c] benzazepin-3- ones 9. The high product yields and the ease of the reactions under surprisingly mild conditions are particularly intriguing in view of the complex mechanistic pathway involved in the overall transformation. A mechanism based on a multistep rearrangement is proposed, ...