title: Preparation of 3-diazoindolin-2-imines via cascade reaction between indoles and sulfonylazides and their extensions to 2,3-diaminoindoles and imidazo[4,5-b]indoles.
abstract: 3-Diazoindolin-2-imines were constructed from indoles and sulfonylazides via an electronically matched 1,3-dipolar cycloaddition and a subsequent dehydroaromatization/ring-opening cascade. The reaction between 3-substituted indoles and sulfonyl azides provided 2-aminoindoles, while 2-substituted indoles furnished 3-aminoindoles. Moreover, 2,3-diaminoindoles could be prepared from the resulting 3-diazoindolin-2-imines and secondary amines via a rhodium-catalyzed amination. Further extension of 2,3-diaminoindoles led to the formation of imidazo[4,5-b]indoles.
authors.affiliation: Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
authors.forename: Guorong
authors.initials: G
authors.lastname: Sheng
authors.forename: Kai
authors.initials: K
authors.lastname: Huang
authors.forename: Zhihao
authors.initials: Z
authors.lastname: Chi
authors.forename: Hualong
authors.initials: H
authors.lastname: Ding
authors.forename: Yanpeng
authors.initials: Y
authors.lastname: Xing
authors.forename: Ping
authors.initials: P
authors.lastname: Lu
authors.forename: Yanguang
authors.initials: Y
authors.lastname: Wang
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry
chemical_list: D000588:Amines; D001386:Azides; D006575:Heterocyclic Compounds, 3-Ring; D007093:Imidazoles; D007097:Imines; D007211:Indoles; D012238:Rhodium