31167-21-2Relevant articles and documents
4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil
Sidhoum, Madjid Ait,El Ka?m, Laurent,Grimaud, Laurence
, p. 5222 - 5231 (2018/05/04)
The Ugi-Smiles reaction of S-benzyl thiouracil have been exploited in several three-step sequences for the preparation of aminopyrimidine libraries with high diversity. After the 4-component coupling, oxidation of the thioether to sulfone is followed by displacement of the latter by various carbon-centered nucleophiles (cyanide, malonate, boronic acids) or amines. The efficiency of the whole sequence was further demonstrated with one-pot procedures.
Ugi-smiles coupling of thiouracil derivatives towards 2,4-diamino pyrimidines
Sidhoum, Madjid Ait,Ka?m, Laurent El,Grimaud, Laurence
supporting information; experimental part, p. 632 - 636 (2012/04/11)
Diaminopyrimidines could be synthesized via a multicomponent coupling starting from S-alkyl thiouracil derivatives. The synthetic strategy based upon an Ugi-Smiles coupling, and subsequent oxidation of the adducts affords a versatile platform for the prep
Synthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents
Prachayasittikul, Supaluk,Worachartcheewan, Apilak,Nantasenamat, Chanin,Chinworrungsee, Maneekarn,Sornsongkhram, Nirun,Ruchirawat, Somsak,Prachayasittikul, Virapong
experimental part, p. 738 - 742 (2011/03/20)
Considering that some thiopyrimidines were previously reported as potential therapeutics, the present study achieved novel analogs of bioactive 2-substituted thiopyrimidines-4-(3H)-ones via base catalyzed alkylation reaction of 2-thiouracil using alkyl an
Synthesis of novel 5-phenylselenenyl pyrimidine analogs
Jeelan Basha,Upendar Reddy,Goudgaon
scheme or table, p. 728 - 733 (2010/08/19)
5-Phenylselenenyl-4-substituted-2-benzylthiopyrimidine analogs were prepared efficiently in four steps. Reaction of 2-thiouracil with benzyl chloride in presence of base furnishes 2-benzylthio uracil, which on reaction with phenylselenenyl chloride in pyridine under anhydrous conditions yielded 5-phenylselenenyl-2-benzylthio uracil. Chlorination of 5-phenylselenenyl-2- benzylthio uracil with excess POCl3 under reflux furnishes 5-phenylselenenyl-4-chloro-2-benzylthiopyrimidine. Aromatic nucleophilic substitution reaction of 5-phenylselenenyl-4-chloro-2-benzylthiopyrimidine with oxygen nucleophiles like sodium ethoxide, sodium benzylate and nitrogen nucleophiles like aliphatic primary amines, substituted aromatic primary amines furnished the target compounds in 48-80% yield. 5-Phenylselenenyl-4- (substitutedbenzylidenehydrazino)-2-benzylthiopyrimidines were prepared in 60-75% yield, by the reaction of 5-phenylselenenyl-4-(hydrazino)-2- benzylthiopyrimidine with various aromatic aldehydes.
Cyclization of 4-(2-aminoanilino)-2-benzylthiopyrimidine to novel 1-(2-benzylthiopyrimidin-4-yi)-2-substituted benzimidazoles
Basha, N. Jeelan,Reddy, Ch. Upendar,Goudgaon
body text, p. 469 - 472 (2010/03/04)
1-(2-Benzylthiopyrimiden-4-yl)-2-substituted benzimidazoles 6a-d were prepared efficiently in four steps. Reaction of 2-thiouracil with benzyl chloride in presence of base, furnishes 2-benzylthiouracil 2. This on chlorination with excess POCl3 furnishes 4-chloro-2- benzylthiopyrimidine 3. Compound 3 on reaction with ortho-phenylenediamine via aromatic nucleophilic displacement reaction yielded 4-(2-aminoanilino)-2- benzylthiopyrimidine 4. This on cyclization with CS2 in presence of base furnishes 1-(2-benzylthiopyrimidin-4-yl)-2-thiobenzimidazole 5. Compound 5 on reaction with alkyl, aryl halides and hydrazine hydrate yielded target compounds 6a-d in 52-62% yield.
Development of an efficient and straightforward methodology toward the synthesis of molecularly diverse 2,6-disubstituted 3,4-dihydropyrimidin-4(3H)-ones
Font, David,Heras, Montserrat,Villalgordo, Jose? M.
, p. 1833 - 1842 (2007/10/03)
A simple and efficient methodology toward the synthesis of highly molecularly diverse 2,6-disubstituted 3,4-dihydropyrimidin-4(3H)-ones of type 3 has been developed. The methodology is based on a selective O-alkylation reaction with i-PrOH under Mitsunobu conditions followed by a nucleophilic heteroaromatic ipso-substitution of sulfones 20 and subsequent acidic hydrolysis of the isopropoxy group.
