New efficient synthesis of 1H-imidazo-[4, 5-c]quinolines by a sequential Van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization. Issue 50 (13th December 2018)

• Record Type: Journal Article
• Authors: Guan, Zhi-Rong; Liu, Zi-Ming; Ding, Ming-Wu
• Is Part Of: Tetrahedron. Volume 74:Issue 50(2018)
• Page Start: 7186
• Page End: 7192
• Publication Date: 2018-12-13
• Subjects: 1H-imidazo-[4, 5-c]quinoline -- Van Leusen reaction -- Staudinger reaction -- Aza-Wittig reaction -- Carbodiimide; UNQJVJVIRIBEHJ-UHFFFAOYSA-N -- BEBRKLUTYPRADX-UHFFFAOYSA-N -- GOUCSFXCFWJICP-UHFFFAOYSA-N -- NBWGLALRJWIERK-UHFFFAOYSA-N -- DCKKMCBJRSCYRU-UHFFFAOYSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.10.052
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A new efficient synthesis of multisubstituted 1 H -imidazo-[4, 5- c ]quinoline derivatives via sequential van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization was developed. Azides4, obtained from Van Leusen reaction of 2-azidobenzaldehyde1, amine2 and TosMIC (tosylmethyl isocyanide)3, reacted with triphenyl phosphine to produce iminophosphorane5 . A tandem aza-Wittig reaction of iminophosphorane5 with isocyanate generated 1 H -imidazo-[4, 5- c ]quinoline7 through carbodiimide intermediate6 in moderate to good yield. Graphical abstract: