1034497-95-4Relevant academic research and scientific papers
Trifluoroacetic acid: An efficient catalyst for paal-knorr pyrrole synthesis and its deprotection
Venugopala, K. Narayanaswamy,Prasanna, Renuka T.,Odhav, Bharti
, p. 8685 - 8689 (2013/11/06)
In the present work, we demonstrated a simple and an efficient method for the condensation of substituted aryl/heteroaryl amines with acetonylacetone in the presence of trifluoro acetic acid to afford the corresponding 2,5-dimethyl-1-substitued pyrroles using Paal-Knorr synthesis in excellent yields. Trifluoroacetic acid was used under reflux condition for the deprotection of 2,5-dimethyl-1-substitued pyrroles to their corresponding substituted aryl/heteroaryl amines in moderate yields. 2,5-Dimethyl-1-substitued pyrrole were characterized by NMR and LC-MS. The yield of the compounds was found to be excellent.
Enantioselective Pd-catalyzed α-arylation of N-Boc-pyrrolidine: The key to an efficient and practical synthesis of a glucokinase activator
Klapars, Artis,Campos, Kevin R.,Waldman, Jacob H.,Zewge, Daniel,Dormer, Peter G.,Chen, Cheng-Yi
, p. 4986 - 4993 (2008/12/21)
(Chemical Equation Presented) A short and practical synthesis of glucokinase activator 1 was achieved utilizing a convergent strategy involving SNAr coupling of activated aryl fluoride 11 with hydroxypyridine 9. The key to the success of the synthesis was the development of a novel method for enantioselective formation of α-arylpyrrolidines during the course of the project. In this method, (-)-sparteine-mediated enantioselective lithiation of N-Boc-pyrrolidine was followed by in situ transmetalation to zinc and Pd-catalyzed coupling with aryl bromide 3, proceeding in 92% ee. This transformation allowed the preparation of compound 1 in a 31% overall yield over six steps.
