A3 Coupling Reaction as a Key Strategy in a Three-Step Synthesis of Bioactive Alkaloids

A3 Coupling Reaction as a Key Strategy in a Three-Step Synthesis of Bioactive Alkaloids

Wendler, Edison P.; Carmona, Rafaela C.; Santos, Alcindo A. Dos

Abstract:

In the last decades the multicomponent reactions have been shown to be an important way to prepare high functionalized compounds within high atom-, energy- and step- economy. One of these compounds are the propargylamines, which are important chiral tools in organic synthesis especially in the pharmaceutical industry. This class of compounds are important building blocks for the preparation of complex amino derivatives and bioactive substances. An important known strategy for the synthesis of this class of compounds consists in the 1,2-addition reaction of non-functionalized acetylenic organometallics to a C-N double bond, usually of imines, enamines, nitrones and iminium salts. In this study, we payed attention to develop a three-component one-step coupling, using alkynols, benzylamine and aldehydes to prepare benzylamine propargyl alcohols.

In the last decades the multicomponent reactions have been shown to be an important way to prepare high functionalized compounds within high atom-, energy- and step- economy. One of these compounds are the propargylamines, which are important chiral tools in organic synthesis especially in the pharmaceutical industry. This class of compounds are important building blocks for the preparation of complex amino derivatives and bioactive substances. An important known strategy for the synthesis of this class of compounds consists in the 1,2-addition reaction of non-functionalized acetylenic organometallics to a C-N double bond, usually of imines, enamines, nitrones and iminium salts. In this study, we payed attention to develop a three-component one-step coupling, using alkynols, benzylamine and aldehydes to prepare benzylamine propargyl alcohols.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0205-1

Referências bibliográficas

• [1] 1 Wei, C.; Mague, J. T.; Li, C-J. Proc. Natl. Acad. Sci. USA 2004, 101, 5749-5754.
• [2] 2 a) Zhu, J.; Bienayme, H. Multicomponent Reactions. 1st Ed. Weinheim, Wiley-VCH Verlag GmbH And Co, 2005. b) Zani, L.; Bolm, C. Chem. Commun. 2006, 4263-4275.

Como citar:

Wendler, Edison P.; Carmona, Rafaela C.; Santos, Alcindo A. Dos; "A3 Coupling Reaction as a Key Strategy in a Three-Step Synthesis of Bioactive Alkaloids", p-205-205. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0205-1