TY - JOUR
T1 - Synthesis of 3-Aminoquinazolinones via a SnCl2-Mediated ANRORC-like Reductive Rearrangement of 1,3,4-Oxadiazoles
AU - Elagawany, Mohamed
AU - Maram, Lingaiah
AU - Elgendy, Bahaa
N1 - Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/12/15
Y1 - 2023/12/15
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85179603424&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c01973
DO - 10.1021/acs.joc.3c01973
M3 - Article
C2 - 38016045
AN - SCOPUS:85179603424
SN - 0022-3263
VL - 88
SP - 17062
EP - 17068
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -