Multicomponent catalytic Mannich Reaction: a methodological study with lawsone

V Lacerda Jr,R B Dos Santos,E V R De Castro,R G Fiorot,S G Greco,J F Allochio Filho

doi:10.5151/chempro-15bmos-bmos2013_2013915222817

Abstract

The multicomponent one-pot synthesis has received great importance due to its wide range of applications in pharmaceutical chemistry and combinatorial libraries for drug discovery. The Mannich reaction is a classical method for the preparation of -aminocarbonylated compounds from amine, aldehyde and an active CH bond, and it’s one of the most important reaction in organic chemistry. Our research group described the multicomponent Mannich reaction with lawsone and various aldehydes and amines in ethanol at room temperature, according to the procedure found in the literature with some modifications. It should be noticed that the reaction times ranged from 12 to 48 hours, depending on the aldehyde and the amine used. Dabiri and co-workers published Mannich reaction in aqueous medium, under reflux, using InCl3 as catalyst where reaction times varied from 4 to 7.5 hours.

Highlights

The multicomponent one-pot synthesis has received great importance due to its wide range of applications in pharmaceutical chemistry and combinatorial libraries for drug discovery.1The Mannich reaction is a classical method for the preparation of -aminocarbonylated compounds from amine, aldehyde and an active CH bond, and it’s one of the most important reaction in organic chemistry.Our research group described the multicomponent Mannich reaction with lawsone and various aldehydes and amines in ethanol at room temperature, according to the procedure found in the literature with some modifications.2 It should be noticed that the reaction times ranged from 12 to 48 hours, depending on the aldehyde and the amine used
Multicomponent Mannich reaction derived from lawsone and pirrolydine
Different solvent were screened in order to choose the best one in terms of yield and reaction time (Table 1)

Summary

Introduction

The multicomponent one-pot synthesis has received great importance due to its wide range of applications in pharmaceutical chemistry and combinatorial libraries for drug discovery.1The Mannich reaction is a classical method for the preparation of -aminocarbonylated compounds from amine, aldehyde and an active CH bond, and it’s one of the most important reaction in organic chemistry.Our research group described the multicomponent Mannich reaction with lawsone and various aldehydes and amines in ethanol at room temperature, according to the procedure found in the literature with some modifications.2 It should be noticed that the reaction times ranged from 12 to 48 hours, depending on the aldehyde and the amine used. The multicomponent one-pot synthesis has received great importance due to its wide range of applications in pharmaceutical chemistry and combinatorial libraries for drug discovery.1 The Mannich reaction is a classical method for the preparation of -aminocarbonylated compounds from amine, aldehyde and an active CH bond, and it’s one of the most important reaction in organic chemistry.

Results

Conclusion