Chichibabin pyridinium synthesis. Issue 6 (7th February 2019)

• Record Type: Journal Article
• Authors: Imura, Akiho; Tanaka, Nao; Usuki, Toyonobu
• Is Part Of: Tetrahedron letters. Volume 60:Issue 6(2019)
• Page Start: 489
• Page End: 492
• Publication Date: 2019-02-07
• Subjects: Chichibabin pyridinium synthesis -- Tetrasubstituted pyridinium -- Pr(OTf)3 -- Aldol condensation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.01.011
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Mechanistic studies of Chichibabin pyridinium synthesis were examined. Interesting pyridinium skeleton was formed under several conditions. GC–MS analysis of intermediate aldol condensate was carried out. Abstract: Chichibabin pyridine synthesis involves the reaction of three aldehydes and ammonia to form 2, 3, 5-trisubstituted pyridines. This study examined the synthesis of tetrasubstituted pyridinium from aldehydes and an amine hydrochloride in the presence/absence of Pr(OTf)3 . Important insights into the reaction mechanisms of Chichibabin pyridinium synthesis were proposed through the investigation of reaction intermediates along with quantitative GC–MS analysis.