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Semi-synthesis of imidazo-5α-hydroxyvouacapane from Caesalpinia pulcherrima via a Groebke−Blackburn−Bienaymé reaction
1, 2 , 3 , 4 , 2 , 2 , 2 , * 3
1  laboratorio de Diseño Molecular, Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo. Ciudad Universitaria, C.P. 58030, Morelia, Michoacán, México
2  laboratorio de Productos Naturales, Instituto de Investigaciones Químico Biológicas, Universidad Michoaca-na de San Nicolás de Hidalgo. Ciudad Universitaria, C.P. 58030, Morelia, Michoacán, México
3  Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria, Morelia C.P. 58030, Michoacán, Mexico;
4  laboratorio de Diseño Molecular, Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo. Ciudad Universitaria, C.P. 58033, Morelia, Michoacán, México
Academic Editor: Julio A. Seijas

Abstract:

A semi-synthetic strategy and operationally simple to obtain a new heterocyclic system imidazo-5α-hydroxyvouacapane in two-step reactions was developed. The first reaction step is a Vilsmeier-Haack formylation at the furan ring of the 5α-hydroxyvouacapane isolated from Caesalpinia pulcherrima stems to obtain the 5α-hidroxyvouacapane-aldehyde in 33% yield. The second reaction step is a Groebke−Blackburn−Bienaymé reaction to synthesize the imidazo-5α-hydroxyvouacapane by using 2-aminopyridine and tert-buthyl isocyanide in 75% yield. This work contributes significantly to semi-synthesis through multicomponent reactions, an area with limited literature coverage.

Keywords: 5α-hydroxyvouacapane; Groebke−Blackburn−Bienaymé reaction; Caesalpinia pulcherrima; isocyanides; semi-synthesis
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