AlCl3-catalyzed insertion of isocyanides into nitrogen-sulfur bonds of sulfenamides

被引：9
|
作者：
Shiro, Daisuke [1 ]
Fujiwara, Shin-ichi [2 ]
Tsuda, Susumu [2 ]
Iwasaki, Takanori [1 ]
Kuniyasu, Hitoshi [1 ]
Kambe, Nobuaki [1 ]
机构：
[1] Osaka Univ, Grad Sch Engn, Suita, Osaka 5650871, Japan
[2] Osaka Dent Univ, Dept Chem, Hirakata, Osaka 5731121, Japan
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 12期
关键词：
Insertion; Sulfenamide; Isocyanide; Isothiourea; Lewis acid; VICARIOUS NUCLEOPHILIC-SUBSTITUTION; NITRIC-OXIDE SYNTHASES; ONE-POT SYNTHESIS; AMINYL RADICALS; SYNTHETIC PRECURSORS; ALPHA-SULFENYLATION; CYCLIC SULFENAMIDES; ISOTHIOUREAS; ALKYL; 1,4-BENZOTHIAZEPINES;
D O I：
10.1016/j.tetlet.2015.01.096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lewis acid-catalyzed insertion of isocyanides 2 into nitrogen-sulfur bonds of sulfenamides 1 was developed. This method provided a convenient method for the synthesis of isothioureas 3. Among Lewis acids examined, AlCl3 brought about the best result. Acetic acid assisted one-pot preparation of unsymmetrical ureas was also described. (C) 2015 Published by Elsevier Ltd.
引用
收藏
页码：1531 / 1534
页数：4
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