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: jlaha
niper.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 40°C 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
