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

[Display omitted] 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 pr...

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Published inTetrahedron letters Vol. 56; no. 12; pp. 1531 - 1534
Main Authors Shiro, Daisuke, Fujiwara, Shin-ichi, Tsuda, Susumu, Iwasaki, Takanori, Kuniyasu, Hitoshi, Kambe, Nobuaki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.03.2015
Elsevier
Subjects
Chemistry
Chemistry, Organic
Insertion
Isocyanide
Isothiourea
Lewis acid
Physical Sciences
Science & Technology
Sulfenamide
Lewis acid
Insertion
Sulfenamide
Isothiourea
Isocyanide
VICARIOUS NUCLEOPHILIC-SUBSTITUTION
ALKYL
ONE-POT SYNTHESIS
1,4-BENZOTHIAZEPINES
ISOTHIOUREAS
SYNTHETIC PRECURSORS
NITRIC-OXIDE SYNTHASES
ALPHA-SULFENYLATION
AMINYL RADICALS
CYCLIC SULFENAMIDES
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.01.096