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- Title
Synthesis of Indolyl‐1,3‐dienes from β‐Sulphonyl Aldehydes through One‐Pot Sequential Brønsted Acid/Base Catalysis.
- Authors
Karan, Ganesh; Sahu, Samrat; Sudan Maji, Modhu
- Abstract
Introduction of a 1,3‐diene moiety at the C3‐position of pyrrole and indole bearing various aliphatic as well as aromatic functional groups with good stereoselectivity remains a challenging task. Keeping the synthetic applicability in mind, an eccentric strategy is developed to synthesize 1,3‐dienyl pyrroles and indoles from unprotected pyrroles and indoles employing β‐sulphonyl aldehyde as a dienylating agent. This method is developed by using a one‐pot sequential Brønsted acid/base catalysis strategy. The nucleophilicity of indole is transmitted through the conjugation to eliminate the sulfonyl groups in a step‐wise manner. Further, this developed protocol was extended to the incorporation of a 1,3,5‐triene moiety at the C3‐position of indoles through unprecedented successive three sulfonyl group elimination. As an application of this strategy, a Diels−Alder reaction and hydrothiolation of 1,3‐diene were demonstrated.
- Subjects
BRONSTED acids; SULFONYL group; ALDEHYDES; CATALYSIS; DIELS-Alder reaction; SCHIFF bases; SULFONYL compounds
- Publication
European Journal of Organic Chemistry, 2022, Vol 2022, Issue 18, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202200240