α-卤代醛酮和硫脲在中性无水溶剂条件下关环得到2-胺基噻唑的反应。硫代酰胺和α-卤代醛酮也可以关环得到2取代噻唑。

反应机理

反应实例

2-(Phenylamino)-4-methylthiazole (3). To a stirred suspension of anhyd MgSO4 (1 g) in acetone (15 mL) containing N-phenylthiourea 1 (2.5 g, 16.4 mmol), was added dropwise a solution of chloroacetone 2 (1.52 g, 16.4 mmol) in anhyd acetone (15 mL) under reflux. After 1 h stirring under reflux, the mixture was cooled, poured into brine (80 mL) and basified with 18 M ammonia. Extraction with Et2O and evaporation of the solvent afforded 2.97 g (96%) of crude 3. Recrystallization from MeOH gave 2.1 g (68%) of 3 as a first crop, mp 86–87 ℃ and 0.72 g (23%) of a second crop of 3, mp 85–86 ℃.

【Meakins GD, J Chem Soc Perkin 1, 1987, 1, 639】

相关文献

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2 Sharma GM J Ind Chem Soc 1967 57 44

3 Arakawa K Chem Pharm Bull 1972 20 1041

4 Birkinshaw TN J Chem Soc Perkin 1 1982 1 939

5 Meakins GD J Chem Soc Perkin 1 1987 1 639

6 Meyers AI Tet Lett 1994 35 2473

7 Goodnow RA Jr Org Lett 2001 3 3655

8 Erian AW Molecules 2003 8 793

9 Bautista D J Org Chem 2006 71 5328

10 Singh SP Syn Comm 2007 37 2501

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 202.