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- W2143200785 abstract "Abstract 2‐Acyl‐ N ‐propargylindoles 1 and 2‐acyl‐3‐propargylindoles 5 undergo aminobenzannulation reactions with pyrrolidine in the presence of an appropriate Lewis acid to give 9‐aminopyrido[1,2‐ a ]indoles 6 and 1‐aminocarbazoles 7 , respectively. The selection of the appropriate Lewis acid, TiCl 4 or GaCl 3 for 1 and InCl 3 for 5 , allows the domino process involving the initial formation of an enamine intermediate, followed by a regioselective 6‐ exo ‐ dig intramolecular nucleophilic attack of the nucleophilic terminus of the unsaturated system (the β‐carbon of the enamino moiety) to the carbon–carbon triple bond. Moreover, several features concerning the reaction mechanism and the role of both catalysts, in connection with the electronic properties of the reacting alkynes, are reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)" @default.
- W2143200785 created "2016-06-24" @default.
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- W2143200785 creator A5061679724 @default.
- W2143200785 creator A5071903769 @default.
- W2143200785 date "2009-05-26" @default.
- W2143200785 modified "2023-09-25" @default.
- W2143200785 title "Lewis Acid Mediated Aminobenzannulation Reactions of δ‐Ketoalkynes: Synthesis of 1‐Aminocarbazoles and 9‐Aminopyrido[1,2‐<i>a</i>]indoles" @default.
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- W2143200785 doi "https://doi.org/10.1002/ejoc.200900039" @default.
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