A solvent-free and catalyst-free reaction of o-aminobenzophenone with aryl isothiocyanates: expedient access to congested 4-phenyl-4-hydroxyquinazolin-2-thione derivatives

Le Anh Nguyen; Thi Thu Tram Nguyen; Quoc Anh Ngo; Pascal Retailleau; Thanh Binh Nguyen

doi:10.1039/d4ob01452a

A solvent-free and catalyst-free reaction of o-aminobenzophenone with aryl isothiocyanates: expedient access to congested 4-phenyl-4-hydroxyquinazolin-2-thione derivatives

Org Biomol Chem. 2024 Dec 11;22(48):9353-9356. doi: 10.1039/d4ob01452a.

Authors

Le Anh Nguyen^{1

2}, Thi Thu Tram Nguyen³, Quoc Anh Ngo¹, Pascal Retailleau⁴, Thanh Binh Nguyen⁴

Affiliations

¹ Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam. [email protected].
² Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
³ Department of Chemistry, Faculty of Science, Can Tho University of Medicine and Pharmacy, Vietnam.
⁴ Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av de la Terrasse, 91198 Gif-sur-Yvette, France. [email protected].

PMID: 39480663
DOI: 10.1039/d4ob01452a

Abstract

An efficient method to construct 4-phenyl-4-hydroxyquinazolin-2-thiones 3via solvent-free and catalyst-free addition of o-aminobenzophenone 1 with aryl isothiocyanates 2 under thermal conditions has been developed, providing new congested 4-phenyl-4-hydroxyquinazolin-2-thiones 3 in practically quantitative yields via simple purification by filtration/recrystallization. Extension of these conditions to o-aminoacetophenone 4 in place of o-aminobenzophenone 1 led to 4-methylenequinazoline-thione 5 as a result of a subsequent dehydration reaction.