α-卤代羰基化合物与硫氢化钠在原位反应产生的α-巯基羰基化合物直接与另一羰基化合物组分和氨反应生成噻唑啉的反应。1956年由德国化学家 Friedrich Asinger 在苏联发现。反应中生成的α-巯基羰基化合物会和按反应生成α-巯基亚胺，因此可以得到α-巯基亚胺的反应都可以通过此反应得到产物。

一分子酮先形成亚胺，重排为烯胺，接着单质硫进行α位取代得到α-巯基亚胺中间体。

α-巯基胺也可以进行此反应，不过要加入氧化剂。

反应机理

反应实例

【Martens J, Tet Lett., 2000, 41, 7289】

10,6-Dimethyl-20,40,50,60,70,70a-hexahydrospiropiperidine-4,2-thiazolo-[5,4-c]-pyridine 2HCl (2).

A stirred and ice cooled suspension of sulfur (6.0 g, 187 mmol) in 1-methyl-4-piperidone 1 (40 g, 354 mmol) was treated with a flow of NH3 maintaining the temperature between 40–50 C until all traces of sulfur disappeared. The excess of NH3 was removed in vacuo, the mixture was diluted with 50% K2CO3 solution (200 mL) and extracted with ether (5  100 mL). The dried solution was treated

with dry HCl. The solid was filtered, washed (Et2O) and dried in vacuo to give 53.5 g of 2.2HCl (97%), mp 200–205 C, after crystallization mp 240 C.

【Lyle RE, J Org Chem., 1965, 30, 293】

相关文献

1 Asinger F Liebigs Ann 1957 602 37

2 Asinger F Liebigs Ann 1957 606 67

3 Asinger F Angew Chem 1958 70 372

4 Asinger F Liebigs Ann 1964 674 57

5 Lyle RE J Org Chem 1965 30 293

6 Domling A Tetrahedron 1995 51 755

7 Martens J Tet Lett 2000 41 7289

8 Dunach E Tet Asymm 2001 12 1279

9 Offermanns H Angew Chem Int 2007 46 6010

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 13.