Synthesis of 2-Acyltryptamines through an Unexpected Brønsted Acid Catalyzed Formal 1,5-Migration of Functional Group
Yao Lei1, Zi-Yan Wu1, Pei-Sen Zou1
1Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi), School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin, 541004, China.
Abstract:
Herein, we have developed a Brønsted acid catalyzed 1,5-migration of functional groups from indole-tethered ynamides to prepare a variety of 2-acyltryptamines in good to excellent yields with high site-selectivity at the C2-position of indoles. Mechanistic studies revealed that the reaction underwent an intramolecular cyclization, 1,2-migration of the vinyl group, and C-N bond cleavage by hydrolysis in a one pot. The reaction features broad substrate scope, good functional group compatibility, 1,5-migration of functional groups, Csp-N bond cleavage to form Csp2-Csp2 bond, and diverse 2-acyltryptamine scaffolds.
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