Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines. Issue 39 (30th September 2015)

• Record Type: Journal Article
• Authors: Giles, Robert G.; Heaney, Harry; Plater, M. John
• Is Part Of: Tetrahedron. Volume 71:Issue 39(2015)
• Page Start: 7367
• Page End: 7385
• Publication Date: 2015-09-30
• Subjects: Indole(s) -- Pyrrole(s) -- Ketones -- Secondary amines; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.05.005
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Reactions of N -methyl- and N -ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines. Graphical abstract: