A Strecker approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates. Issue 16 (20th April 2016)

• Record Type: Journal Article
• Authors: Cheng, Ken; McClory, Andrew; Walker, Whitney; Xu, Jie; Zhang, Haiming; Angelaud, Remy; Gosselin, Francis
• Is Part Of: Tetrahedron letters. Volume 57:Issue 16(2016)
• Page Start: 1736
• Page End: 1738
• Publication Date: 2016-04-20
• Subjects: Thiazole -- Strecker -- Convergent -- Thioamide -- Cyanide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.12.069
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A general approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates is reported herein. Both aliphatic and aromatic thioamides undergo 1, 2-addition to ethyl glyoxylate to give hemiaminals which, when treated with acetyl chloride, undergo elimination to the corresponding imines. Upon exposure to aqueous sodium cyanide the imines undergo a Strecker addition–cyclization reaction to provide the target heterocycles in modest to good yields over the 3-step process.