Hantzsch reaction with 6-aminouracil: Synthesis of novel tetrakis(6-aminouracil-5-yl)methanes and bis(decahydropyrido[2,3-d:6,5-d']dipyrimidine-tetraones) linked to aliphatic or aromatic cores via ether-amide or ester-amide linkages
Abstract:One-pot three-component cyclo-condensation reaction of bis(aldehydes) containing ether-amide or esteramide linkages with 6-aminouracil in boiling acetic acid afforded tetrakis(6-aminopyrimidine-2,4-diones) or bis (tetraoxodecahydropyrido[2,3-d:6,5-d']dipyrimidines) depending on the reaction conditions.
“…28 Furthermore, acridines have attracted considerable attention due to their reported bioactivities. [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43] In conjunction with these findings, and in continuation of our recent project aimed at the synthesis of novel bis(heterocyc les), [44][45][46][47][48][49][50][51][52][53][54][55] we report herein on the one-pot synthesis of novel bis(acridines), bis(dipyrazolo[3,4-b:4′,3′-e]pyridines), and bis(pyrimido [4,5-b]quinolines) incorporating thieno [2,3-b] thiophenes through ether or ester bridges.…”
A novel series of bis(hexahydroacridine-1,8-diones), bis(tetrahydrodipyrazolo[3,4- b:4′,3′- e]pyridines), and bis(pyrimido[4,5- b]quinolines) incorporating a thieno[2,3- b]thiophene core via ether or ester linkages is prepared via a Hantzsch-like reaction.
“…28 Furthermore, acridines have attracted considerable attention due to their reported bioactivities. [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43] In conjunction with these findings, and in continuation of our recent project aimed at the synthesis of novel bis(heterocyc les), [44][45][46][47][48][49][50][51][52][53][54][55] we report herein on the one-pot synthesis of novel bis(acridines), bis(dipyrazolo[3,4-b:4′,3′-e]pyridines), and bis(pyrimido [4,5-b]quinolines) incorporating thieno [2,3-b] thiophenes through ether or ester bridges.…”
A novel series of bis(hexahydroacridine-1,8-diones), bis(tetrahydrodipyrazolo[3,4- b:4′,3′- e]pyridines), and bis(pyrimido[4,5- b]quinolines) incorporating a thieno[2,3- b]thiophene core via ether or ester linkages is prepared via a Hantzsch-like reaction.
“…Abdelmoniem et al [ 83 ] synthesized bis (pyridodipyrimidine-tetraones) through one-pot multicomponent reactions. Thus, the reactions of bis (aldehydes) with four equivalents of 6-amino-uracil in acetic acid at reflux temperature furnished tetrakis(6-aminopyrimidine-2,4-diones) 47 or bis (pyrido-dipyrimidines) 48 as controlled by the reaction conditions.…”
Section: Synthetic Approachesmentioning
confidence: 99%
“…Next, Michael's addition step took place for another two molecules of 6-amino-uracil to the intermediates F-2 formed compounds 47 . The pyridine ring cyclization was achieved by the release of ammonia molecules through intramolecular cyclization supported by p -TSA to give the products 48 [ 83 ]. Scheme 25 The projected mechanism for the synthesis of bis -pyridodipyrimidines …”
The entitled review aimed to assemble and highlight the synthetic approaches and biological aspects of heterocycles with pyridodipyrimidine motifs. The recent synthetic approaches were categorized according to the accomplishments of the approaches under catalyst or catalyst-free conditions. The topic involved the synthesis of substituted tricyclic systems and spirocyclic systems. The present study offered an overview of the recent literature in addition to a scope of the preceding literature. The proposed mechanisms of the varied target products were discussed. Pyridodipyrimidine displayed potential and privileged cytotoxic, antioxidant, and antimicrobial performances. The competitions, challenges, and prospects are also deliberated.
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