Synthesis of 3-Aminoquinazolinones via a SnCl2-Mediated ANRORC-like Reductive Rearrangement of 1,3,4-Oxadiazoles

Mohamed Elagawany; Lingaiah Maram; Bahaa Elgendy

doi:10.1021/acs.joc.3c01973

Synthesis of 3-Aminoquinazolinones via a SnCl₂-Mediated ANRORC-like Reductive Rearrangement of 1,3,4-Oxadiazoles

J Org Chem. 2023 Dec 15;88(24):17062-17068. doi: 10.1021/acs.joc.3c01973. Epub 2023 Nov 28.

Authors

Mohamed Elagawany^{1

2

3}, Lingaiah Maram^{1

2}, Bahaa Elgendy^{1

2

4}

Affiliations

¹ Center for Clinical Pharmacology, Washington University School of Medicine and University of Health Sciences and Pharmacy, St. Louis, Missouri 63110, United States.
² Department of Pharmaceutical and Administrative Sciences, University of Health Sciences and Pharmacy, St. Louis, Missouri 63110, United States.
³ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Damanhour University, Damanhour 22516, Egypt.
⁴ Chemistry Department, Faculty of Science, Benha University, Benha 13518, Egypt.

PMID: 38016045
DOI: 10.1021/acs.joc.3c01973

Abstract

Herein, we developed a new SnCl₂-mediated ANRORC (addition of nucleophile, ring-opening, and ring-closure)-like rearrangement for the synthesis of 3-amino-2-substituted-quinazolin-4(3H)-one from 2-(2-nitrophenyl)-5-substituted-1,3,4-oxadiazole. The new method is solvent-dependent and features the use of a green solvent system (i.e., ethanol/water), high yields, and simple workup. The reduced product could be exclusively synthesized by changing the solvent to acetonitrile.