Iodine Catalyzed Oxidative Synthesis of Quinazolin-4(3H)-ones and Pyrazolo[4,3-d]pyrimidin-7(6H)-ones via Amination of sp(3) C-H Bond

Molecular iodine catalyzed oxidative coupling of 2-aminobenzamides with aryl methyl ketones produced 2-aryl quinazolin-4(3H)-ones. The reaction performed well in the absence of any metal or ligand. The quantity of iodine played a very crucial role in this transformation in order to selectively get 2...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-07, Vol.80 (13), p.6915-6921
Main Authors: Mohammed, Shabber, Vishwakarma, Ram A, Bharate, Sandip B
Format: Article
Language:English
Subjects:
Amination
Catalysis
Hydrogen Bonding
Iodine - chemistry
Molecular Structure
Oxidation-Reduction
Quinazolinones - chemistry
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Summary:Molecular iodine catalyzed oxidative coupling of 2-aminobenzamides with aryl methyl ketones produced 2-aryl quinazolin-4(3H)-ones. The reaction performed well in the absence of any metal or ligand. The quantity of iodine played a very crucial role in this transformation in order to selectively get 2-aryl quinazolin-4(3H)-ones. The utility of this protocol for synthesis of pyrazolo[4,3-d]pyrimidin-7(6H)-ones including a key intermediate involved in sildenafil synthesis has also been demonstrated.
ISSN:1520-6904
DOI:10.1021/acs.joc.5b00989