Synthesis of Novel Phenylselenenyl Disubstituted…新型苯基苯基二取代苯乙烯的合成.pdfVIP

Chem Sci Trans., 2012, 1(1), 210-216 Chemical Science Transactions DOI:10.7598/cst2012. 127 ISSN: 2278-3458 RESEARCH ARTICLE Synthesis of Novel 5-Phenylselenenyl-2,4-Disubstituted Pyrimidine Analogs * ISMAIL, UPENDAR REDDY CH and THALARI GANGADHAR Department of Chemistry, Nizam College, Bhasheerbhagh, Hyderabad-500001, Andhra Pradesh, India gangadhar.thalari@ Received 6 May 2012 / Accepted 18 May 2012 Abstract: 5-Phenylselenenyl-2,4-disubstituted pyrimidine analogs were prepared efficiently in four steps. Thiol group of 2-thiouracil was protected with various alkylating agents in presence of base furnishes 2-alkylthiouracils (2a-c), these on reaction with phenylselenenyl chloride in pyridine under anhydrous conditions yielded 5-phenylselenenyl-2-alkylthiouracils (3a-c). Chlorination of 5-phenyl-selenenyl-2- alkylthiouracils with excess POCl3 under reflux furnishes 5-phenylselenenyl-4-chloro-2- alkylthiopyrimidines (4a-c). Aromatic nucleophilic substitution reaction of 5-phenyl-selenenyl-4-chloro- 2-alkylthiopyrimidines with oxygen nucleophiles like sodium phenoxides furnished the target compounds (5a-o) in 60-75% yield. All the synthesized compounds were evaluated for antimicrobial activities. Keywords: Pyrimidine analogs, 2-Alkyllthiouracils, 5-Phenylselenenylpyrimidines, 2,4,5-Trisubstituted pyrimidines Introduction Selenium, an essential trace mineral1 is a vital component of the selenoproteins specifically glutathione peroxidase mainly required for normal health and reproduction2 . Selenium was discovered in 1818 by Swedish chemist Berzelius. It was considered as a poison until it was identified as a micronutrient fo