Selective Synthesis of 2-(1,2,3-Triazoyl) Quinazolinones through Copper-Catalyzed Multicomponent Reaction

Manoela Sacramento,Raquel G Jacob,Luís Pedro A Piúma,Diego Alves,Eder João Lenardão,José Edmilson R Nascimento,Roberta Cargnelutti

doi:10.3390/catal11101170

Abstract

We describe here our results from the copper-catalyzed three component reaction of 2-azidobenzaldehyde, anthranilamide and terminal alkynes, using Et3N as base, and DMSO as solvent. Depending on the temperature and amount of Et3N used in the reactions, 1,2,3-triazolyl-quinazolinones or 1,2,3-triazolyl-dihydroquinazolinone could be obtained. When the reactions were performed at 100 °C using 2 equivalents of Et3N, 1,2,3-triazolyl-dihydroquinazolinone was formed in 82% yield, whereas reactions carried out at 120 °C using 1 equivalent of Et3N provided 1,2,3-triazolyl-quinazolinones in moderate-to-good yields.

Highlights

Nitrogen heterocyclic compounds are among the most representative chemical architectures, and they are found in several natural products and commercial drugs
The quinazolinones are synthesized by the condensation of o-aminobenzamides with aldehydes [10], phenylacetic acid [11] and alcohols [12,13]
Continuing our studies on the synthesis of new functionalized 1,2,3-triazoles, and due to the pharmacological importance of the 1,2,3triazoyl-quinazolinones scaffold, we describe the synthesis of a range of new 2(1,2,3-triazoyl)quinazolin-4(3H)-ones by a copper-catalyzed multicomponent reaction of

Summary

Introduction

Nitrogen heterocyclic compounds are among the most representative chemical architectures, and they are found in several natural products and commercial drugs. Quinazolinones are important members of the N-heterocycles, and they are building blocks in numerous natural products and widely used in the preparation of synthetic bioactive compounds, especially in the pharmaceutical industry [1]. Quinazolinones derivatives exhibit a wide range of pharmacological activities, including antimicrobial and antitubercular [2], anti-inflammatory [3], antiviral [4], anticancer [5], anti-Alzheimer [6], antimalarial [7], among others [8,9] (Figure 1). The quinazolinones are synthesized by the condensation of o-aminobenzamides with aldehydes [10], phenylacetic acid [11] and alcohols [12,13]. Other important protocols include carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes [14], oxidative annulation of alcohols with o-aminoarylnitriles [15], and Cu-catalyzed oxidative annulation of anilines, alkylamines and aldehydes [16]

Objectives

Methods

Results

Conclusion