The Application of Arylglyoxals in the Synthesis of Pyrrolo[2,3-d]pyrimidines via Multicomponent Reactions

Abstract

This review provides an overview of the recent literature on application of arylglyoxals the synthesis of pyrrolo[2,3-d]pyrimidines via multicomponent reactions in the period of 2008-2018. 1,2-Dicarbonyl compounds are attractive precursors for synthesis of various heterocyclic compounds, and arylglyoxals are frequently applied in synthesis of various organic compounds, and in particular of pyrrolo[2,3-d]pyrimidines derivatives, which are important due to their biological and pharmaceutical activities.

Magnetic Silica-Coated Picolylamine Copper Complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)]-Catalyzed Biginelli Annulation Reaction

“…Eco-friendly and cost-effective procedures like selectivity, simple reaction methods, no use of column chromatography, high efficiency, and high yield of products have been considered as an important subject in organic synthesis. Therefore, the formation and development of carbon–carbon and carbon-heteroatom bonds by employing multicomponent reactions (MCRs) are the most important subject to the synthesis of chemotherapeutic drugs and organic compounds by one-pot reaction. − MCRs are defined by one-pot synthesis, in which the desired product is obtained from a number of various starting materials (for instance, three or more reactants). MCRs have received significant attention in organic synthesis both environmentally and economically compared with multistep synthesis due to various advantages such as simple separation steps, lower energy costs, less waste, excellent yield, short reaction time, and cost-effective.…”

Recent applications of aminouracil in multicomponent reactions

“…90 In another study, this group reported an efficient procedure for the reaction of arylglyoxals ( 9) with 6amino-1,3-dimethyluracil (2) and 4-hydroxycoumarin (33), in the presence of L-proline in acetic acid under reflux conditions, affording polyfunctionalized pyrrolo [2,3-d] Recently, the synthesis of polyfunctionalized pyrrolo [2,3-d]pyrimidine derivatives was reported in a review. 49…”

“…This method proved to be of considerable utility to researchers to obtain desired complex heterocyclic frameworks by condensation of more than two reactants in a single operational step. [41][42][43][44][45][46][47][48] Herein, in continuation of studies towards the synthesis of heterocyclic scaffolds via multicomponent reactions, [49][50][51][52] and because the 6-aminouracil is frequently used as a starting material in synthesizing these compounds. This review is devoted to recent applications of 6-aminouracil and its derivatives in synthesizing diverse heterocyclic compounds based on MCRs from 2015 to 2020.…”

Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

“…111 Recently, the synthesis of polyfunctionalized pyrrolo [2,3-d]pyrimidine derivatives was reported in a review. 70 Chen and coworkers have reported the multicomponent synthesis of N-bridgehead-fused pyrroles 98 and 99 by reaction of arylglyoxals 4, cyclohexane-1,3-diones 31, and heterocyclic ketene aminals 97 under two different reflux conditions in high yield (Scheme 40). 112 Scheme 40.…”