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Keywords = 8-aryl-3-methyl-2-methylthiopurine-6-ones

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14 pages, 310 KiB  
Article
Novel 2-Thioxanthine and Dipyrimidopyridine Derivatives: Synthesis and Antimicrobial Activity
by Samar El-kalyoubi, Fatmah Agili and Shaker Youssif
Molecules 2015, 20(10), 19263-19276; https://doi.org/10.3390/molecules201019263 - 22 Oct 2015
Cited by 11 | Viewed by 6381 | Correction
Abstract
Several fused imidazolopyrimidines were synthesized starting from 6-amino-1-methyl-2-thiouracil (1) followed by nitrosation, reduction and condensation with different aromatic aldehydes to give Schiff’s base. The dehydrocyclization of Schiff’s bases using iodine/DMF gave Compounds 5ag. The methylation of 5a [...] Read more.
Several fused imidazolopyrimidines were synthesized starting from 6-amino-1-methyl-2-thiouracil (1) followed by nitrosation, reduction and condensation with different aromatic aldehydes to give Schiff’s base. The dehydrocyclization of Schiff’s bases using iodine/DMF gave Compounds 5ag. The methylation of 5ag using a simple alkylating agent as dimethyl sulfate ((CH3)2SO4) gave either monoalkylated imidazolopyrimidine 6ag at room temperature or dialkylated derivatives 7ag on heating 6ag with ((CH3)2SO4). On the other hand, treatment of 1 with different aromatic aldehydes in absolute ethanol in the presence of conc. hydrochloric acid at room temperature and/or reflux with acetic acid afforded bis-5,5́-diuracylmethylene 8ae, which cyclized on heating with a mixture of acetic acid/HCl (1:1) to give 9ae. Compounds 9ae can be obtained directly by refluxing of Compound 1 with a mixture of acetic acid/HCl. The synthesized new compounds were screened for antimicrobial activity, and the MIC was measured. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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