Davidson恶唑合成反应
α-羟基酮先和酰氯反应生成α-羟酰基酮，接着与乙酸铵或氨脱水关环生成恶唑的反应。除了中间体3，氰醇酯也可以进行此反应。
反应机理
反应操作
2-Methyl-4,5-diphenyloxazole (4). A mixture acetylbenzoin 3 (6.35 g), ammonium acetate (10 g), and HOAc (25 mL) was refluxed for 1 h. The reaction mixture was treated with water (100 mL) and extracted with PhH (3 25 mL). Workup and vacuum distillation afforded 4.8 g (82%) of 4 as a viscous oil, bp 210–213 C/18 mm.
【Davidson D, J Org Chem, 1937, 2, 328】
相关文献
1 Davidson D J Org Chem 1937 2 328
2 Willey RH Chem Rev 1945 37 401
3 Theiling S Chem Ber 1953 86 96
4 Cornforth JW J Chem Soc 1953 93
5 Budevich M Chem Ber 1954 87 700
6 Rangnekar DW Dyes Pigments 1989 10 69
7 Whitney SE J Org Chem 1991 56 3058
8 Beletskii EV Russ J Org Chem 2009 45 1229
相关反应
Bredereck噁唑合成法(Bredereck Oxazole Synthesis)
康福斯重排反应(Cornforth Rearrangement)
编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 116.