Synthesis 2022; 54(14): 3162-3179
DOI: 10.1055/a-1794-8355
short review

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

a   Departamento de Química, CCE, Universidade Federal de Viçosa, Viçosa, MG, 36570-900, Brazil
,
b   Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil
,
Ângelo de Fátima
b   Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil
,
Sergio Antonio Fernandes
a   Departamento de Química, CCE, Universidade Federal de Viçosa, Viçosa, MG, 36570-900, Brazil
› Author Affiliations
All studies performed by the groups of de Fátima and Fernandes on Povarov reactions were financially supported by the Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), and the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) (Financial Code 01). A.F. and S.A.F. are supported by CNPq Research Fellowships


Abstract

The multicomponent Povarov reaction represents a powerful approach for the construction of substances containing N-heterocyclic frameworks. By using the Povarov reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines in a single step, it is possible to form the following new bonds: two Csp 3–Csp 3 and one Csp 3–Nsp 3, two Csp 2–Csp 2 and one Csp 2–Nsp 2, and four Csp 3–Csp 3 and two Csp 3–Nsp 1, respectively. This short review discusses the main features of the Povarov reaction, including its mechanism, the reaction scope by employing different catalysts and substrates, as well as stereoselective versions.

1 Introduction

2 Mechanism of the Povarov Reaction

3 Tetrahydroquinolines

4 Quinolines

5 Julolidines

6 Concluding Remarks



Publication History

Received: 31 December 2021

Accepted after revision: 10 March 2022

Accepted Manuscript online:
10 March 2022

Article published online:
17 May 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany