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Oxidative Aza-Annulation of Enynyl Azides to 2-Keto/Formyl-1H-pyrroles

Chada Raji Reddy* , Sujatarani A. Panda and Andhavaram Ramaraju

*Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500607, India, Email: rajireddyiict.res.in

C. R. Reddy, S. A. Panda, A. Ramaraju, J. Org. Chem., 2017, 82, 944-949.

DOI: 10.1021/acs.joc.6b02468 (free Supporting Information)



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Abstract

An intramolecular oxidative aza-annulation of enynyl azides provides pyrroles bearing a 2-keto or formyl group via sequential carbon-nitrogen/carbon-oxygen bond formations in the presence of catalytic amounts of AuCl3 and AgSbF6. The required enynyl azides are readily prepared from Morita-Baylis-Hillman (MBH) acetates of acetylenic aldehydes.

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proposed mechanism



Note

Under inert atmosphere using dry solvent, there was no progress in the reaction

Raji Reddy, November 11, 2017


Key Words

pyrroles


ID: J42-Y2017