Synthesis of Substituted Oxazoles from N‐Benzyl Propargyl Amines and Acid Chlorides. Issue 21 (6th June 2013)

• Record Type: Journal Article
• Authors: v. Wachenfeldt, Henrik; Paulsen, Filip; Sundin, Anders; Strand, Daniel
• Is Part Of: European journal of organic chemistry. Issue 21(2013)
• Page Start: 4578
• Page End: 4585
• Publication Date: 2013-06-06
• Subjects: Synthetic methods -- Cycli­zation -- Heterocycles -- Microwave chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300285
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The reaction between N ‐benzylpropargylamines and acid chlorides at elevated temperatures provides efficient, direct access to a variety of di‐ and tri‐substituted oxazoles. The versatility of this reaction is explored and 21 examples are demonstrated. The usefulness of the methodology is showcased through the short and efficient formal syntheses of medicinally relevant drugs aleglitazar and romazarit. Abstract : The reaction between N ‐benzylpropargylamines and acid chlorides at elevated temperatures gives oxazoles in up to 99 % yield. Twenty‐one examples are demonstrated varying the substitution at all positions of the heterocycle.