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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

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Author(s):
Prediger, Patricia [1] ; da Silva, Allan Ribeiro [1] ; Duarte Correia, Carlos Roque [1]
Total Authors: 3
Affiliation:
[1] Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Tetrahedron; v. 70, n. 20, p. 3333-3341, MAY 20 2014.
Web of Science Citations: 18
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 beta,beta-diaryl propionate that was converted to tolpropamine. (C) 2013 Elsevier Ltd. All rights reserved. (AU)

FAPESP's process: 11/23832-6 - New methodological and mechanistic studies related to the Heck arylations employing arenediazonium salts and synthetic applications
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Regular Research Grants