Site-Selective Deoxygenative Amination of Azine N-Oxides with Carbodiimides under Catalyst-, Activator-, Base-, and Solvent-Free Conditions

Bikash Kumar Sarmah, Monuranjan Konwar and Animesh Das*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, 781039, India, Email: adasiitg.ac.in

B. K. Sarmah, M. Konwar, A. Das, J. Org. Chem., 2021, 86, 10762-10772.

DOI: 10.1021/acs.joc.1c00741

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Abstract

A [3+2] dipolar cycloaddition of azine N-oxide withs carbodiimides provides 2-amino azines smoothly under simple heating conditions without any transition metal catalyst, activator, base, and solvent. This transformation demonstrates a broad substrate scope and produces CO₂ as the only co-product.

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proposed mechanistic pathways

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Key Words

Quinolines

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ID: J42-Y2021