Sulfate Radical Anion (SO4•-) Mediated C(sp³)-H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

Joydev K. Laha*, K. S. Satyanarayana Tummalapalli, Akshay Nair and Nidhi Patel

*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, K. S. S. Tummalapalli, A. Nair, N. Patel, J. Org. Chem., 2015, 80, 11351-11359.

DOI: 10.1021/acs.joc.5b01872

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Abstract

A transition-metal-free, K₂S₂O₈-mediated intramolecular oxidative nitrogenation/oxygenation of C(sp³)-H in N-aryl benzylic amines followed by oxidation at the benzylic center provides an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones.

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Key Words

quinazolinones, potassium peroxydisulfate

ID: J42-Y2015

Sulfate Radical Anion (SO4•-) Mediated C(sp3)-H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

Joydev K. Laha*, K. S. Satyanarayana Tummalapalli, Akshay Nair and Nidhi Patel

Sulfate Radical Anion (SO4•-) Mediated C(sp³)-H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles