Two Different Green Catalytic Systems for One‐Pot Regioselective and Chemoselective Synthesis of Some Pyrimido[4,5‐d]Pyrimidinone Derivatives in Water

Abstract

In this work, we have developed green and efficient regioselective and chemoselective syntheses of 5‐aryloyl‐1,3‐dimethyl‐7‐thioxo‐5,6,7,8‐tetrahydropyrimido[4,5‐d]pyrimidine‐2,4(1H,3H)‐dione and 5‐aryloyl‐1,3‐dimethyl‐2,7‐dithioxo‐2,3,5,6,7,8‐hexahydropyrimido[4,5‐d]pyrimidin‐4(1H)‐one derivatives via one‐pot three‐component Biginelli‐like condensation of arylglyoxal monohydrates, N,N‐dimethylbarbituric acid or N,N‐dimethyl‐2‐thiobarbituric acid, and thiourea in water at 50°C. The presence of two different green catalytic systems (ZrOCl2.8H2O and also DABCO) proceeded efficiently to afford the desired products in good‐to‐excellent yields. An aqueous reaction medium, high regioselectivity and chemoselectivity, simple operation and suitable yields of products are the important features of these green protocols.

A green and practical one‐pot two‐step strategy for the synthesis of symmetric 3,6‐diarylpyridazines

“…As part of our ongoing efforts toward the development of new synthetic methods for important heterocyclic frameworks, herein, we report a one‐pot two‐step process for the synthesis of symmetric 3,6‐diarylpyridazine derivatives using a three‐component reaction of aryl methyl ketones, arylglyoxal monohydrates, and hydrazine hydrate. This new method is green, simple, and efficient, which can be extended to the synthesis of many other important symmetric and asymmetric 3,6‐diarylpyridazine scaffolds (Scheme ).…”

Green and efficient one-pot three-component synthesis of novel drug-like furo[2,3-d]pyrimidines as potential active site inhibitors and putative allosteric hotspots modulators of both SARS-CoV-2 MPro and PLPro

“…Zirconium IV oxychloride octahydrate (ZrOCl 2 •8H 2 O), as an available, low-cost, easy handling, and moisture-stable catalyst with highly coordinating ability, has attracted the attention in the organic synthetic community. [23] In the past two decades, the mentioned green catalyst has been used frequently in various organic transformations, especially heterocyclic ones, including syntheses of 4 H -chromenes, [24] pyrimido [4] , [5] , [6] , [7] , [8] , [9] , [10] , [11] , [12] , [13] , [14] , [15] , [16] , [17] , [18] , [19] , [20] , [21] , [22] , [23] , [24] , [25] , [26] , [27] , [28] , [29] , [30] , [31] , [32] , [33] , [34] , [35] , [36] , [37] , [38] , [39] , [40] , [41] , [42] , [43] , [44] , [45] , [46] , [47] , [48] , [49] , [50] , [51] , [52] , [53] , [54] , [55] , [56] , [57] pyrimidinones, [25] dibenzo[ b , i ]xanthene-tetraones, [26] , [1] , [3] oxazino [5] , [6] ,…”

Novel edaravone-based azo dyes: efficient synthesis, characterization, antibacterial activity, DFT calculations and comprehensive investigation of the solvent effect on the absorption spectra

“…24 Dyes based on 5-pyrazolone, are especially extensively used in color photographic materials. [25][26][27] In the context of our general interest in the synthesis of heterocyclic compounds, [28][29][30][31][32][33][34][35][36][37][38][39][40][41] herein, we propose a facile synthesis of the new dyes based on edaravone due to the unique properties of this compound. The synthesis of the desired compounds is possible through the coupling reaction of azo compounds with edaravone (D1-D10).…”