M. Tolba, A. El-Dean, Mostafa Ahmed
Nov 25, 2018
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0
Influential Citations
10
Citations
Journal
Journal of the Chinese Chemical Society
Abstract
Pyrimidine and thienopyrimidine derivatives play a very important role in organicchemistry because of their wide applications as bioactive compounds with multiplebiological activities. However, a literature survey revealed that the merger of differ-ent groups in the thieno[2,3-d]pyrimidine heterocyclic ring enhances its antibacter-ial, antifungal and antiinflammatory activities. This encouraged us to prepare anew series of thieno[2,3-d]pyrimidi ne heterocyclic compounds and to test them asantimicrobial and anti-inflammatory agents. These compounds have shown remark-able activity toward fungi, bacteria, and inflammation. Thus, these compoundshave been prepared by the chloroacylation of 5-amino-4-phenyl-2-(ptolylamino)thieno[2,3-d] pyrimidine-6-carboxamide (4) using chloroacetyl chloride under neatcondition to afford the target compound (6 ), which was used as precursor for thesynthesis of a number of bioactive compounds. Thus reaction of the chloromethy l-pyrimidine derivative (6) with triphenylphosphine in dry benzene gave the corre-sponding ((4-oxo-9-phenyl-7-(p-tolylamino)-3,4-dihydropyrimido[40,50:4,5]thieno[2,3-d]pyrimidin-2-yl)methyl) triphenylphosphonium chloride (7). Compounds 8a–8c and 9a–9c were obtained by the reaction of 7 with some selected aromatic alde-hydes and ketones in methanol and sodium methoxide under Wittig reaction condi-tion.