An unexpected synthesis of β-amino-α-mesyl-γ-sultams upon mesylation of hindered α-aminonitriles

被引：5

作者：

Dyachenko, Maksim S. ^{[1
,2
]}

Dobrydnev, Alexey V. ^{[1
,2
]}

Chuchvera, Yaroslav O. ^{[1
,2
]}

Shishkina, Svitlana V. ^{[3
,4
]}

Volovenko, Yulian M. ^{[2
]}

机构：

[1] Enamine Ltd, 78 Chervonotkatska St, UA-02094 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, 60 Volodymyrska St, UA-01601 Kiev, Ukraine

[3] Natl Acad Sci Ukraine, State Sci Inst, Inst Single Crystals, 60 Nauky Ave, UA-61001 Kharkiv, Ukraine

[4] Kharkov Natl Univ, Dept Inorgan Chem, 4 Svobody Sq, UA-61077 Kharkiv, Ukraine

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2020年 / 56卷 / 03期

关键词：

aminonitriles; spiro compounds; sulfonamides; cyclization; X-ray study; INHIBITORS; CYCLIZATION; 1,3-PROPANESULTAMS; 2,2-DIOXIDES; DERIVATIVES; ANALOGS; SYSTEM; TSAO;

D O I：

10.1007/s10593-020-02671-y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report one-pot procedure for an unexpected synthesis of previously unknown 4-amino-5-methylsulfonyl-2,3-dihydroisothiazole 1,1-dioxides (also called beta-amino-alpha-mesyl-gamma-sultams). Thus, the reaction of mesyl chloride with hindered alpha-aminonitriles is accompanied by the formation of interim N-(1-cyanoalkyl)(methylsulfonyl)methanesulfonamides which, in turn, undergo the carbanion-mediated sulfonate (sulfonamido) intramolecular cyclization reaction yielding beta-amino-alpha-mesyl-gamma-sultams. The structure of the title compounds was confirmed by X-ray diffraction study. The proposed mechanistic insights of the reaction are in accordance with the results of additional experiments and literature data.

引用

页码：386 / 391

页数：6