Greener Synthesis of Pyrroloquinazoline Derivatives: Recent Advances

Abstract

Quinazoline derivatives draw attention from a synthetic and medicinal chemistry point of view, given the wide range of biological activities already described. This class of fused Nheterocyclic compounds has also shown its importance and potential pharmacological application. This Review covers the contributions reported in the last ten years for the synthesis of pyrroloquinazoline derivatives, focusing on greener protocols to obtain these adducts, such as multicomponent reactions, photocatalysis, microwaves, electrosynthesis among others.

Copper-Catalyzed Synthesis of Pyrrolo[1,2-c]quinazolines and Pyrrolo[2,1-a]isoquinolines and Antiplasmodial Evaluation

“…Moreover, there are few reports in the literature describing the synthesis of pyrroloquinazolines starting from quinazolines . Due to their relevant biological activities, the search for environmentally more benign methods for the synthesis of these scaffolds has attracted attention in recent years …”

Cyclizations of Alkenyl(Alkynyl)‐Functionalized Quinazolinones and their Heteroanalogues: A Powerful Strategy for the Construction of Polyheterocyclic Structures

“…[56] Quinazolin-4-ones and their heteroanalogues are thus potent pharmacophores, which are extensively harnessed in the design of biologically relevant substances and drugs. It is for biomedically oriented design purposes that synthetic methodologies have been elaborated to construct new pyrimidineheteroannulated, [57][58][59] hetaryl-substituted [10] and hybrid polyheterocyclic nuclei, [10,26,27,60] as an alternative to the initial quinazolinone core. Among annulated polyheterocycles, 2,3fused quinazolinones deserve special attention, as they constitute the framework of natural and synthetic compounds with diverse bioactivity such as the anticancer agent deoxyvasicinone 1, [61] the cholinesterase inhibitor (antidemential) mackinazolinone 2, [62] the broad-spectrum pharmacological agent, in particular, bronchodilator, anti-inflammant and antimicrobial vasicinone 3, [63] and the anti-inflammant isaindi-gotone 4 [64] (Figure 1).…”

“…[69] Most of the strategies for the construction of heteroannulated quinazolinones are based on two main synthetic approaches: 1) tandem cyclizations of o-aminobenzoic acid derivatives; 2) intramolecular cyclizations of functionalized quinazolinones, which have been well documented in recent review articles. [57,58] However, it should be noted that summarized evidence on the use of alkenyl(alkynyl)quinazolinones as cyclization substrates is focused mainly on 3-substituted derivatives, whereas their 2-substituted analogues are only briefly addressed in the mini-review. [59] It appears therefore reasonable to systematically…”

“…Most of the strategies for the construction of heteroannulated quinazolinones are based on two main synthetic approaches: 1) tandem cyclizations of o‐aminobenzoic acid derivatives; 2) intramolecular cyclizations of functionalized quinazolinones, which have been well documented in recent review articles [57,58] …”