Synthesis

Facile synthesis of 3-carbamoyl-1, 2, 4-oxadiazoles

M Tamura, Y Ise, Y Okajima, N Nishiwaki, M Ariga

Index: Tamura, Mina; Ise, Yumiko; Okajima, Yoshikazu; Nishiwaki, Nagatoshi; Ariga, Masahiro Synthesis, 2006 , # 20 p. 3453 - 3461

Full Text: HTML

Citation Number: 0

Abstract

Abstract A range of 1, 2, 4-oxadiazoles, having a carbamoyl group at the 3-position, were synthesized from 2-methyl-4-nitroisoxazolin-5 (2H)-one via three steps. Ammonolysis of this nitroisoxazolone afforded 2-amino-2-hydroxyimino-N-methylacetamide in excellent yield. O- Acylation of this key amidoxime, followed by ring closure, proceeded smoothly to give 3- carbamoyl-1, 2, 4-oxadiazoles having a substituent at the 5-position which could be easily ...