The Journal of Organic Chemistry

The reaction of oxalyl chloride with amides. II. Oxazolidinediones and acyl isocyanates

AJ Speziale, LR Smith

Index: Speziale,A.J.; Smith,L.R. Journal of Organic Chemistry, 1963 , vol. 28, p. 1805 - 1811

Full Text: HTML

Citation Number: 106

Abstract

The reaction of oxalyl chloride with N-monosubstituted amides has been shown to yield aryloxamic arid chlorides or 2-methyleneoxazolidine-4, 5-diones depending on the structure of the amide and experimental conditions. Treatment of primary amides with oxalyl chloride was found to be a general preparation of acyl isocyanates. A mechanism for the reaction of oxalyl chloride with various amides is discussed.

Related Articles:

CD4 mimics targeting the HIV entry mechanism and their hybrid molecules with a CXCR4 antagonist

[Narumi, Tetsuo; Ochiai, Chihiro; Yoshimura, Kazuhisa; Harada, Shigeyoshi; Tanaka, Tomohiro; Nomura, Wataru; Arai, Hiroshi; Ozaki, Taro; Ohashi, Nami; Matsushita, Shuzo; Tamamura, Hirokazu Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 19 p. 5853 - 5858]

Reactivity of carbamoyl radicals. A new, general, convenient free-radical synthesis of isocyanates from monoamides of oxalic acid

[Minisci, Francesco; Fontana, Francesca; Coppa, Fausta; Yan, Yong Ming Journal of Organic Chemistry, 1995 , vol. 60, # 17 p. 5430 - 5433]

Synthesis and biological evaluation of novel oxalamido derivatives as caspase-3 inhibitors

[Sengupta, Saumitra; Rao, G. Venkateshwar; Dubey Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011 , vol. 50, # 7 p. 901 - 905]

More Articles...