Iodine promoted dual oxidative C(sp3)-H amination of 2-methyl-3-arylquinazolin-4(3H)-ones: a facile route to 1,4-diarylimidazo[1,5-a]quinazolin-5(4H)-ones

Kavitha Donthiboina; Hari Krishna Namballa; Siddiq Pasha Shaik; Jagadeesh Babu Nanubolu; Nagula Shankaraiah; Ahmed Kamal

doi:10.1039/c7ob02677c

Iodine promoted dual oxidative C(sp³)-H amination of 2-methyl-3-arylquinazolin-4(3H)-ones: a facile route to 1,4-diarylimidazo[1,5-a]quinazolin-5(4H)-ones

Org Biomol Chem. 2018 Mar 7;16(10):1720-1727. doi: 10.1039/c7ob02677c.

Authors

Kavitha Donthiboina¹, Hari Krishna Namballa, Siddiq Pasha Shaik, Jagadeesh Babu Nanubolu, Nagula Shankaraiah, Ahmed Kamal

Affiliation

¹ Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad-500 037, India. shankar@niperhyd.ac.in.

PMID: 29457816
DOI: 10.1039/c7ob02677c

Abstract

An iodine promoted tandem oxidative condensation of benzylamines and 2-methylquinazolin-4-(3H)-ones was developed to yield imidazo[1,5-a]quinazolin-5(4H)-ones via dual C(sp³)-H amination under metal free conditions in a greener way using molecular oxygen as a terminal oxidant. This tandem transformation provides an efficient approach to construct various functionalized imidazo[1,5-a]quinazolin-5(4H)-ones in a straightforward manner via a sequential amination-oxidation-annulation-aromatisation.