Part of this work was presented at the 233rd ACS Meeting, March, 25–29, 2007, Chicago, IL, USA, ORGN-316.
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Full Paper
Design and Synthesis of 1-Benzazepine Derivatives by Strategic Utilization of Suzuki–Miyaura Cross-Coupling, Aza-Claisen Rearrangement and Ring-Closing Metathesis†
Article first published online: 17 DEC 2007
DOI: 10.1002/ejoc.200700921
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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How to Cite
Kotha, S. and Shah, V. R. (2008), Design and Synthesis of 1-Benzazepine Derivatives by Strategic Utilization of Suzuki–Miyaura Cross-Coupling, Aza-Claisen Rearrangement and Ring-Closing Metathesis. Eur. J. Org. Chem., 2008: 1054–1064. doi: 10.1002/ejoc.200700921
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Publication History
- Issue published online: 6 FEB 2008
- Article first published online: 17 DEC 2007
- Manuscript Received: 28 SEP 2007
Funded by
- Department of Science and Technology (DST). Grant Number: SR/S1/OC-42-2004
- Industrial Research & Consultancy Centre, IIT-Bombay. Grant Number: 06RPA002
- Council for Scientific and Industrial Research (CSIR)
- Abstract
- Article
- References
- Cited By
Keywords:
- Aza-Claisen rearrangement;
- 1-Benzazepine;
- Cross-coupling;
- Metathesis
Abstract
A new and simple methodology has been realized for the synthesis of 7-substituted 2,3,4,5-tetrahydro-1-benzazepine derivatives with Suzuki–Miyaura cross-coupling, aza-Claisen rearrangement and ring-closing metathesis (RCM) the key steps. Here, o-allylacetanilide derivatives were obtained by Suzuki–Miyaura cross-coupling of the corresponding o-iodoacetanilides. The o-allylacetanilides, on N-allylation under phase-transfter catalysis conditions, provided diallyl derivatives as suitable precursors for RCM. These diallyl derivatives, on treatment with Grubbs' second-generation catalyst, gave the 1-benzazepine derivatives in moderate-to-good yields. These RCM products were found to be unstable and so they were hydrogenated to provide stable tetahydro-1-benzazepine derivatives 25–28. 1H-1-Benzazepin-2-one derivatives 44 and 45 were synthesized following a similar sequence. In addition, the aza-Claisen rearrangement was utilized as a key step in the preparation of RCM precursor 17. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)