New efficient synthesis of 1H-imidazo-[4,5-c]quinolines by a sequential Van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization |
| |
| Authors: | Zhi-Rong Guan Zi-Ming Liu Ming-Wu Ding |
| |
| Institution: | Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan, 430079, PR China |
| |
| Abstract: | A new efficient synthesis of multisubstituted 1H-imidazo-4,5-c]quinoline derivatives via sequential van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization was developed. Azides 4, obtained from Van Leusen reaction of 2-azidobenzaldehyde 1, amine 2 and TosMIC (tosylmethyl isocyanide) 3, reacted with triphenyl phosphine to produce iminophosphorane 5. A tandem aza-Wittig reaction of iminophosphorane 5 with isocyanate generated 1H-imidazo-4,5-c]quinoline 7 through carbodiimide intermediate 6 in moderate to good yield. |
| |
| Keywords: | Van Leusen reaction Staudinger reaction Aza-Wittig reaction Carbodiimide UNQJVJVIRIBEHJ-UHFFFAOYSA-N BEBRKLUTYPRADX-UHFFFAOYSA-N GOUCSFXCFWJICP-UHFFFAOYSA-N NBWGLALRJWIERK-UHFFFAOYSA-N DCKKMCBJRSCYRU-UHFFFAOYSA-N |
| 本文献已被 ScienceDirect 等数据库收录！ |
