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Diversity in Heterocycle Synthesis Using α-Iminocarboxylic Acids: Decarboxylation Dichotomy

Joydev K. Laha* and Mandeep Kaur Hunjan

*Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research, S. A. S. Nagar, Punjab 160062, India, Email: jlahaniper.ac.in

J. K. Laha, M. K. Hunjan, J. Org. Chem., 2022, 87, 2315-2323.

DOI: 10.1021/acs.joc.1c02110


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Abstract

Reactions of ortho-substituted anilines and arylglyoxylic acids in DMSO at 40C provide various benzo-fused five- to six-membered N-heterocycles in very good yields. The reaction proceeds via intramolecular Michael addition of α-iminocarboxylic acids, generated in situ, with an ortho-substituted nucleophile, followed by decarboxylation forms the N-heterocycles.

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hypothesis and experimental findings

synthesis of Sildenafil



Key Words

benzimidazoles, benzothiazoles


ID: J42-Y2022