One-pot synthesis of methyl 4-amino-2,3,3-trisubstituted-1,1-dioxo-2,3-dihydro-1H-1λ6- isothiazole-5-carboxylates

被引：15

作者：

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

Vashchenko, Bohdan V. ^{[1
]}

Konovalova, Iryna S. ^{[3
]}

Bisikalo, Kyrylo O. ^{[1
]}

Volovenko, Yulian M. ^{[1
]}

机构：

[1] Taras Shevchenko Natl Univ Kiev, Dept Chem, Lva Tolstoho St 12, UA-01033 Kiev, Ukraine

[2] SMC Ecopharm Ltd, Naberezhno Korchuvatska St 136-B, UA-03045 Kiev, Ukraine

[3] Natl Acad Sci Ukraine, Div Funct Mat Chem, SSI Inst Single Crystals, Nauky Ave 60, UA-61001 Kharkov, Ukraine

来源：

MONATSHEFTE FUR CHEMIE | 2018年 / 149卷 / 10期

关键词：

Sulfonamides; CSIC reaction; Spiro compounds; Alkyl carboxylates; Aminonitriles; Cyclization; X-ray structure determination; ALPHA-AMINONITRILES; CYCLOADDITION REACTION; FUSED 1,2-DITHIOLES; ANALOGS; ACID; DERIVATIVES; 1,1-DIOXIDES; INHIBITORS; CATALYST; OXIDES;

D O I：

10.1007/s00706-018-2241-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A range of aminonitriles, readily available by Strecker reaction, were forced to react with methyl 2-(chlorosulfonyl) acetate. Methyl 2-[[(cyanoalkyl) amino] sulfonyl] acetates formed on the first stage without isolation were converted to methyl 4-amino-2,3,3-trisubstituted-1,1-dioxo-2,3-dihydro-1H-1 lambda(6) -isothiazole-5-carboxylates via CSIC reaction using Et3N-mediated conditions in poor to high yields. The structure of the target compound was confirmed by X-ray diffraction study.

引用

页码：1827 / 1833

页数：7

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