One‐pot Synthesis of Fully Substituted Pyrimidines Using Amidine and Ketene Dithioacetals as Synthons and Their Antimicrobial Activity

Abstract

A simple, convenient, and efficient one‐pot synthesis of fully substituted pyrimidines was developed by cyclocondensation of α‐oxo ketene dithioacetals with amidine in the presence of potassium carbonate in good yield. Structures of all the newly synthesized compounds were elucidated by elemental analysis and spectral analysis. All the newly synthesized compounds are tested toward different microorganisms.

One-Pot Sequential Approach for the Construction of Highly Functionalized Triazolo[4,3-c]pyrimidine Library

“…1,2-dihydropyrimidine-5-carboxamide 3. 2 To a suspension of 4-isopropoxybenzimidamide 2 (1 mmol) and α-oxo ketene dithioacetals 1 (1 mmol) in dioxane (15mL), dry potassium carbonate (4 mmol) was added, and the reaction mixture was refluxed for appropriate time (Table 1) with constant stirring. After completion of the reaction, the reaction mixture was cooled to room temperature and poured in cold water.…”

“…- [1,2,4]triazolo [4,3-c] 165. 25, 161.22, 160.73, 160.62, 151.52, 148.03, 146.94, 136.19, 134.11, 131.30, 131.00, 129.59, 123.29, 120.86, 119.59, 114.75, 113.50, 109.04, 70.16, 55.41, 31.39, 21.94, 21.85, 21. 5-(4-isopropoxyphenyl)-7-isopropyl-N, 3-di-p-tolyl-[1,2,4]triazolo [4,3-c] 77, 164.70, 163.17, 161.28, 157.46, 135.36, 134.71, 130.83, 129.91, 128.45, 125.51, 120.53, 115.66, 70.16, 34.02, 22.19, 21.14 , 6.40; N, 13.48;found: C, 73.34; H, 6.72; N, 13.93.…”

“…25, 161.22, 160.73, 160.62, 151.52, 148.03, 146.94, 136.19, 134.11, 131.30, 131.00, 129.59, 123.29, 120.86, 119.59, 114.75, 113.50, 109.04, 70.16, 55.41, 31.39, 21.94, 21.85, 21. 5-(4-isopropoxyphenyl)-7-isopropyl-N, 3-di-p-tolyl-[1,2,4]triazolo [4,3-c] 77, 164.70, 163.17, 161.28, 157.46, 135.36, 134.71, 130.83, 129.91, 128.45, 125.51, 120.53, 115.66, 70.16, 34.02, 22.19, 21.14 , 6.40; N, 13.48;found: C, 73.34; H, 6.72; N, 13.93. 3-(2,5-dimethoxyphenyl)-5-(4-isopropoxyphenyl)-7isopropyl-N-(p-tolyl)- [1,2,4]triazolo [4,3-c] 39, 161.35, 160.32, 153.70, 151.67, 150.06, 148.79, 144.48, 136.24, 134.10, 130.35, 129.60, 123.49, 120.91, 117.87, 117.38, 115.63, 113.92, 110.77, 109.09, 70.17, 56.26, 54.98, 31.46, 22.84, 22.15, 21.86, 21.15, 21. , 6.24; N, 12.38; found: C, 71.64; H, 5.88; N, 12.06. (3-bromophenyl)-5-(4-isopropoxyphenyl)-7isopropyl-N-(p-tolyl)- [1,2,4]triazolo [4,3-c] (400 MHz,160.98,151.89,147.80,145.60,136.06,134.25,132.77,132.68,131.03,129.62,129.04,128.10,123.11,121.91,120.89,114.97,109.29,70.36,31.48,21.01,21.94,21.15 5.17; N, 11.98; found: C, 63.92; H, 5.28; N, 12.24.…”

“…3-(2,5-dimethoxyphenyl)-5-(4-isopropoxyphenyl)-7isopropyl-N-(p-tolyl)- [1,2,4]triazolo [4,3-c] 39, 161.35, 160.32, 153.70, 151.67, 150.06, 148.79, 144.48, 136.24, 134.10, 130.35, 129.60, 123.49, 120.91, 117.87, 117.38, 115.63, 113.92, 110.77, 109.09, 70.17, 56.26, 54.98, 31.46, 22.84, 22.15, 21.86, 21.15, 21. , 6.24; N, 12.38; found: C, 71.64; H, 5.88; N, 12.06. (3-bromophenyl)-5-(4-isopropoxyphenyl)-7isopropyl-N-(p-tolyl)- [1,2,4]triazolo [4,3-c] (400 MHz,160.98,151.89,147.80,145.60,136.06,134.25,132.77,132.68,131.03,129.62,129.04,128.10,123.11,121.91,120.89,114.97,109.29,70.36,31.48,21.01,21.94,21.15 5.17; N, 11.98; found: C, 63.92; H, 5.28; N, 12.24. 3-(4-cyanophenyl)-5-(4-isopropoxyphenyl)-7isopropyl-N-(p-tolyl)- [1,2,4]triazolo [4,3-c] 165.95, 164.82, 163.96, 162.34, 151.14, 148.90, 138.48, 137.65, 134.29, 133.76, 133.10, 132.25, 132.16, 130.08, 126.10, 122.72, 121.48, 121.03, 118.79, 115.44, 32.44, 21.89, 20.16, 19.43…”

“…(3-bromophenyl)-5-(4-isopropoxyphenyl)-7isopropyl-N-(p-tolyl)- [1,2,4]triazolo [4,3-c] (400 MHz,160.98,151.89,147.80,145.60,136.06,134.25,132.77,132.68,131.03,129.62,129.04,128.10,123.11,121.91,120.89,114.97,109.29,70.36,31.48,21.01,21.94,21.15 5.17; N, 11.98; found: C, 63.92; H, 5.28; N, 12.24. 3-(4-cyanophenyl)-5-(4-isopropoxyphenyl)-7isopropyl-N-(p-tolyl)- [1,2,4]triazolo [4,3-c] 165.95, 164.82, 163.96, 162.34, 151.14, 148.90, 138.48, 137.65, 134.29, 133.76, 133.10, 132.25, 132.16, 130.08, 126.10, 122.72, 121.48, 121.03, 118.79, 115.44, 32.44, 21.89, 20.16, 19.43…”