Application of 7-endo trig Pictet-Spengler cyclization to the formation of benzazepine ring: Synthesis of new benzazepinoindoles
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Sharma, S K
Sharma, Sunil Agarwal, P K Kundu, Bijoy |
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| Date |
2010-09-09T08:56:55Z
2010-09-09T08:56:55Z 2009 |
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| Identifier |
Eur. J. Org. Chem. 2009(9), 1309-1312
http://hdl.handle.net/123456789/603 |
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| Description |
The preparation of benzazepinoindoles, a fused heterocycles with a benzazepine moiety was realised via an intramolecular 7-endo trig Pictet-Spengler cyclization. The precursors comprising C-3- or C-2-linked o-aminobenzyl indoles (5 and 6) required for the cyclization were obtained by treating either indoles with o-nitrobenzyl bromide followed by reduction of the nitro group or by treating 2-nitrophenylacetic acid with DCC/DMAP followed by reduction of the aryl nitro functionality. The resulting substrates 5 and 6 were then subjected to the 7-endo trig Pictet-Spengler reaction with a variety of aldehydes and ketones to furnish new polycyclic structures benzazepinoindoles.
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| Format |
56595 bytes
application/pdf |
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| Language |
en
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| Subject |
Pictet-Spengler reaction
Fused-ring systems Benzazepine 7-endo trig cyclization polycycles |
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| Title |
Application of 7-endo trig Pictet-Spengler cyclization to the formation of benzazepine ring: Synthesis of new benzazepinoindoles
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| Type |
Article
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