Synthesis of pyrroloazepines. Facile synthesis of 2-substituted pyrrole derivatives by the phosgene method
✍ Scribed by Hidetsura Cho; Shinsuke Matsuki; Akira Mizuno; Hirokazu Annoura; Toshio Tatsuoka
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1997
- Tongue
- English
- Weight
- 375 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
A highly convenient method for the synthesis of 2‐substituted pyrrole derivatives 7a‐c from pyrrole using phosgene was developed. Successively, 7‐methyl‐6,7‐dihydro‐1__H__,5__H__‐pyrrolo[2,3‐c]azepine‐4,8‐dione 1a and 6,7‐dihydro‐1__H__,5__H__‐pyrrolo[2,3‐c]azepine‐4,8‐dione 1b (aldisin) were synthesized by phosphorus pentoxide/methanesulfonate and polyphosphoric acid cyclization.
📜 SIMILAR VOLUMES
Substituted pyrrole derivatives are prepared by treatment of 2,3-dihydrofuran derivatives with trifluoroacetic acid. These in turn are obtained by Michael addition of carbon nucleophiles of the b-dicarbonyl type to N-(4-toluenesulfonyl)-N-(tertbutyloxycarbonyl)-dehydroalanine methyl ester.
## Abstract A facile three‐step synthesis of 2‐(2‐aminophenyl)pyrrole (**1**) and 2‐[(2‐aminomethyl)phenyl]pyrrole (**2**) is reported by use of Suzuki coupling of __N__‐Boc‐pyrrol‐2‐yl boronic acid (**3**) and o‐substituted aryl halogenides, followed by hydrogenation. The Pd‐catalyzed cross‐coupli