Please use this identifier to cite or link to this item:
Type: Artigo de evento
Title: Construction Of 3-arylpropylamines Using Heck Arylations. The Total Synthesis Of Cinacalcet Hydrochloride, Alverine, And Tolpropamine
Author: Prediger P.
Da Silva A.R.
Correia C.R.D.
Abstract: New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck-Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck-Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a very high overall yield (75% over five steps). For alverine, the best results were obtained using a double Heck-Matsuda strategy, providing alverine in an excellent overall yield (69%) from N-acetyl diallylamine in three steps. Tolpropamine was synthesized in a 46% yield over five steps using an efficient reductive Heck-Matsuda arylation between p-bromo-methylcinnamate with 3-chloro tolyldiazonium salt, generating the ,diaryl propionate that was converted to tolpropamine. © 2013 Elsevier Ltd. All rights reserved.
Editor: Elsevier Ltd
Rights: fechado
Identifier DOI: 10.1016/j.tet.2013.10.014
Date Issue: 2014
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
There are no files associated with this item.

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.