Regioselective and stereospecific synthesis of functionalized 3,4-dihydro-2H-1,4-thiazines by catalyst-free [3+3] annulation of pyridinium 1,4-zwitterionic thiolates and aziridines

被引：16

作者：

Wang, Chuan-Chuan ^{[1
]}

Yang, Yan-Tao ^{[2
]}

Wang, Qing-Long ^{[1
]}

Liu, Xue-Hua ^{[3
]}

Chen, Ya-Jing ^{[3
]}

机构：

[1] Henan Univ Anim Husb & Econ, Fac Sci, 146 Yingcai St, Zhengzhou 450044, Henan, Peoples R China

[2] Zhengzhou Univ, Dept Pharm, Affiliated Hosp 1, Zhengzhou 450052, Henan, Peoples R China

[3] Zhengzhou Univ, Sch Pharmaceut Sci, Key Lab Adv Drug Preparat Technol, Minist Educ China, 100 Sci Ave, Zhengzhou 450001, Henan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 16期

关键词：

CYCLOADDITION; DERIVATIVES; CYCLIZATION;

D O I：

10.1039/d2qo00612j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective and stereospecific [3 + 3] annulation between pyridinium 1,4-zwitterionic thiolates and aziridines has been developed, allowing the practical and enantio-retained preparation of functionalized 3,4-dihydro-2H-1,4-thiazines. This reaction proceeds smoothly via a domino S(N)2 ring-opening/N-Michael addition cyclization/retro-Michael addition/Py extrusion procedure under mild conditions without a metal and a strong base. The regioselectivity is greatly affected by the nature of the substituents on aziridines. Moreover, biologically interesting sulfoxide and sulfone analogues could also be conveniently obtained via selective oxidation of the produced 3,4-dihydro-2H-1,4-thiazines using m-CPBA.

引用

页码：4271 / 4276

页数：6

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