Synthesis of pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidines

Synthesis of Pyrazolo[3,4‐d]pyrimidin‐4‐ones Catalyzed by Br?nsted‐acidic Ionic Liquids as Highly Efficient and Reusable Catalysts

“…Prompted by these findings and in line with our research program on synthesis of heterocycles [27][28][29][30][31][32][33][34] and using reusable acid catalysts in organic reactions, [35][36][37][38][39][40][41][42][43][44][45] herein we would like to report a very fast method for the synthesis of pyrazolo [3,4-d]pyrimidin-4-ones through heterocyclization reaction of 5-amino-1H-pyrazole-4-carboxamides with triethyl orthoesters using two Brønsted-acidic ILs, 3-methyl- …”

Synthesis, Characterization and In Vitro Antitumor Evaluation of New Pyrazolo[3,4-d]Pyrimidine Derivatives

“…Structure of the latter was confirmed by the disappearance of the C≡N and NH characteristic absorption bands in the IR spectrum of the starting 5-amino1Hpyrazole-4-carbonitrile 7. Chlorination of compound 8 with phosphorus oxychloride yielded the 4-chloro derivative 9 [19,20]. The latter was allowed to react with different aliphatic and aromatic amines to afford the target pyrazolo [3,4-d]pyrimidin-4-amine derivatives 10 a-e , 11 and 12 (Scheme 2).…”

“…5-Amino-3-(methylthio)-1-phenyl-1H-pyrazole-4-carbonitrile (7) and 3-(methylthio)-1-phenyl-1H-pyrazolo [3,4-d]pyrimidin-4(5H)-one (8) were prepared according to published method 17 . Compound 9 was obtained following reported procedure [19]. 2-chloro-Narylactamide and 3-chloro-N-arylpropanamide derivatives were prepared as reported [24].…”

Dmap-Catalyzed Synthesis of Novel Pyrrolo[2,3-D]Pyrimidine Derivatives Bearing an Aromatic Sulfonamide Moiety

“…DMAP is widely used as a superb nucleophilic catalyst for many organic reactions such as Baylis-Hillman reaction, 29,30 regioselective acylation of 6-O-protected octyl β-D-glucopyranosides, 31 synthesis of electrophilic alkenes, 32 heroin synthesis, 33 and synthesis of N-sulfonyl monocyclic β-lactams. 34 In continuation of our previous works in the synthesis of new heterocyclic compounds with potential biological activities, [35][36][37][38][39][40][41][42][43][44][45] recently, we prepared some new 2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo [2,3-d]pyrimidin-4-amines (derivatives of 7-deazaadenine) by reaction of 2-amino-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitriles with aryl nitriles. 46 In this paper, we report the synthesis of new N-(2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo [2,3-d]pyrimidin-4-yl)benzenesulfonamides 3a-3i in synthetically useful yields by sulfonylation reaction of amino moiety in 2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amines 1a-1c with benzenesulfonyl chlorides 2a-2c in the presence of DMAP with a dual role as a base and also a nucleophilic catalyst under solvent-free conditions (Scheme 1).…”