2-Formylpyrroles as Building Blocks in a Divergent Synthesis of Pyrrolizines

Eder I. Martínez-Mora; Miguel A. Caracas; Carlos H. Escalante; Carlos Espinoza-Hicks; Héctor Quiroz-Florentino; Francisco Delgado; Joaquín Tamariz

doi:10.1055/s-0035-1561331

Synthesis, Table of Contents

Synthesis 2016; 48(07): 1055-1068
DOI: 10.1055/s-0035-1561331

paper

2-Formylpyrroles as Building Blocks in a Divergent Synthesis of Pyrrolizines

Eder I. Martínez-Mora

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N. 11340, México, D.F., Mexico Email: jtamarizm@gmail.com Email: jtamariz@woodward.encb.ipn.mx

,

Miguel A. Caracas

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N. 11340, México, D.F., Mexico Email: jtamarizm@gmail.com Email: jtamariz@woodward.encb.ipn.mx

,

Carlos H. Escalante

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N. 11340, México, D.F., Mexico Email: jtamarizm@gmail.com Email: jtamariz@woodward.encb.ipn.mx

,

Carlos Espinoza-Hicks

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N. 11340, México, D.F., Mexico Email: jtamarizm@gmail.com Email: jtamariz@woodward.encb.ipn.mx

,

Héctor Quiroz-Florentino

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N. 11340, México, D.F., Mexico Email: jtamarizm@gmail.com Email: jtamariz@woodward.encb.ipn.mx

,

Francisco Delgado

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N. 11340, México, D.F., Mexico Email: jtamarizm@gmail.com Email: jtamariz@woodward.encb.ipn.mx

,

Joaquín Tamariz*

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N. 11340, México, D.F., Mexico Email: jtamarizm@gmail.com Email: jtamariz@woodward.encb.ipn.mx

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Abstract

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Abstract

The selective functionalization of 2-formylpyrrole to provide diverse 1,2- and 1,2,5-substituted pyrroles is described. These compounds were used as versatile building blocks in a divergent synthesis of biologically valuable aza-bycyclic skeletons, such as pyrrolizine and pyrrolizidine derivatives. These bicycles were prepared following metal-free cascade synthetic approaches via regioselective intramolecular 1,3-dipolar cycloadditions and stereoselective Knoevenagel/Michael/ cyclization with dimethyl malonate.

Key words

2-formylpyrrole - pyrrolizines - pyrrolizidines - cascade reactions - Knoevenagel/Michael/cyclization

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References

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