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Synthesis of Substituted Thienopyrimidines and Their Evaluation as Antibacterial


Affiliations
1 Department of Pharmaceutical Chemistry, Nargund College of Pharmacy, Dattatreya Nagar, II main, 100 Ft Ring Road, BSK II Stage, Bangalore- 560085, India
2 Department of Chemistry, Texas State University, San Marcos, United States
     

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We have synthesized various substituted thieno(2,3-d)pyrimidines, first by synthesizing ethyl 2-aminothiophene-3- carboxylate (3), by treatment of diethane with ethyl cynoacetate in presence of triethylamine, acetic acid and DMF. Further, the intermediate Ethyl 2-(ethoxycarbonyl)thiophene-3-carboxylate (5) was prepared by compound (3) refluxed with ethyl chloroformate. The key intermediate 3-(3-chloro-4-fluorophenyl) thieno [2, 3-d]pyrimidine-2, 4(1H, 3H)-dione (7) was prepared by cyclisation of compound (5) with 3-chloro-4-fluoro aniline. The nucleophilic substitution of compound 3-(3-chloro-4-fluorophenyl) thieno [2, 3-d]pyrimidine-2, 4(1 H, 3 H)-dione (7) with various aromatic amines(8a-m), aminophenol(8n) gives substituted thienopyrimidines(8a-n). The synthesized new compounds were characterized by MP, TLC, IR and NMR spectra.

Keywords

Thienopyrimidine
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  • Synthesis of Substituted Thienopyrimidines and Their Evaluation as Antibacterial

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Authors

Rahul More
Department of Pharmaceutical Chemistry, Nargund College of Pharmacy, Dattatreya Nagar, II main, 100 Ft Ring Road, BSK II Stage, Bangalore- 560085, India
J. N. Narendra Sharath Chandra
Department of Pharmaceutical Chemistry, Nargund College of Pharmacy, Dattatreya Nagar, II main, 100 Ft Ring Road, BSK II Stage, Bangalore- 560085, India
Shachindra. L. Nargund
Department of Chemistry, Texas State University, San Marcos, United States
L.V.G. Nargund
Department of Pharmaceutical Chemistry, Nargund College of Pharmacy, Dattatreya Nagar, II main, 100 Ft Ring Road, BSK II Stage, Bangalore- 560085, India

Abstract


We have synthesized various substituted thieno(2,3-d)pyrimidines, first by synthesizing ethyl 2-aminothiophene-3- carboxylate (3), by treatment of diethane with ethyl cynoacetate in presence of triethylamine, acetic acid and DMF. Further, the intermediate Ethyl 2-(ethoxycarbonyl)thiophene-3-carboxylate (5) was prepared by compound (3) refluxed with ethyl chloroformate. The key intermediate 3-(3-chloro-4-fluorophenyl) thieno [2, 3-d]pyrimidine-2, 4(1H, 3H)-dione (7) was prepared by cyclisation of compound (5) with 3-chloro-4-fluoro aniline. The nucleophilic substitution of compound 3-(3-chloro-4-fluorophenyl) thieno [2, 3-d]pyrimidine-2, 4(1 H, 3 H)-dione (7) with various aromatic amines(8a-m), aminophenol(8n) gives substituted thienopyrimidines(8a-n). The synthesized new compounds were characterized by MP, TLC, IR and NMR spectra.

Keywords


Thienopyrimidine

References