Catalytic activity of 1,3-dibromo-5,5-dimethylhydantoin (DBH) in the one-pot transformation of N-arylglycines to N-arylsydnones in the presence of NaNO2/Ac2O under neutral conditions:: Subsequent bromination of these sydnones to their 4-bromo derivatives

被引：32

作者：

Azarifar, D ^{[1
]}

Ghasemnejad-Bosra, H ^{[1
]}

机构：

[1] Bu Ali Sina Univ, Dept Chem, Sch Sci, Hamadan 65174, Iran

来源：

SYNTHESIS-STUTTGART | 2006年 / 07期

关键词：

nitrosation; N-arylglycines; sydriones; 1,3-dibromo-5,5-dimethylhydantoin (DBH); bromination;

D O I：

10.1055/s-2006-926380

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO2 and Ac2O in high yields (80-94%) under mild and neutral conditions. Also, it was shown that DBH can conveniently promote the bromination of these sydnones to their 4-bromo substituted congeners in excellent yields in DMF at room temperature.

引用

页码：1123 / 1126

页数：4

共 30 条

[1]

ACKERMAN.E, 1967, PHARMAZIE, V22, P537

[2] 1,3-Dibromo-5,5-dimethylhydantoin as catalyst for the conversion of aldehydes to their 1,1-diacetates (acetylals) under solvent-free and neutral conditions [J].