m-Chloroperbenzoic acid-oxchromium (VI)-mediated cleavage of 2,4,5-trisubstituted oxazoles

TETRAHEDRON LETTERS

卷:58

Article

Patil, Pravin C.¹  Luzzio, Frederick A.¹ 

[1] Univ Louisville, Dept Chem, 2320 South Brook St, Louisville, KY 40292 USA

关键词: Cleavage;    Oxazoles;    Oxochromium (VI);    Peroxides;    Triacylamines;   

DOI  :  10.1016/j.tetlet.2017.02.027

来源: Elsevier

【 摘 要 】

An array of 2-substituted-4,5-diphenyloxazoles were found to be cleaved to triacylamines and diacylamines (imides) using a reagent system composed of m-chloroperbenzoic acid (MCPBA) and 2,2'-bipyridinium chlorochromate (BPCC). The 2-alkyl-4,5-diphenyloxazoles give imides (38-60%) as the predominant cleavage product while the 2-aryl-4,5-diphenyloxazoles give triacylamines (44-71%). Two mechanisms involving intermediates such as cyclic endoperoxides or oxachromacycles were proposed. An application of the oxidative cleavage to the multi-step synthesis of (+/-)-phoracantholide I seco acid is detailed. (C) 2017 Elsevier Ltd. All rights reserved.

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