Application of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) in the solvent free synthesis of (E)-arylidene-1,3-dihydroindole-2-ones

Abstract

An efficient and green condensation reaction is developed for the synthesis of (E)-arylidene-1,3-dihydroindole-2-ones; (1), using heterogeneous nanoporous acid catalyst of SBA-Pr-SO3H with pore size, 6 nm in solvent free condition. Arylidene-1,3-dihydroindole-2-ones have many pharmaceutical properties such as Tyrosin kinase inhibiton. This method has the advantages of short reaction time, isolation ease of the products, excellent yields and recyclable catalyst. Oxindole SBA-Pr-SO3H Green synthesis Solvent free reaction Tyrosin kinase inhibitor Arylidene-1,3-dihydroindole-2-ones

Synthesis of (E)‐3‐Alkylideneindolin‐2‐ones by an Iron‐Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines

“…151-152°C (lit. [21] m.p. 150-152°C); 1 H NMR (400 MHz, CDCl 3 ): δ 9.14 (br s, 1H), 7.82 (s, 1H), 7.68 (d, J = 7.6 Hz, 1H), 7.41-7.37 (m, 1H), 7.27-7.19 (m, 3H), 6.98 (dd, J = 8.4, 2.4Hz, 1H), 6.93 (d,J = 7.6 Hz,1H),1H), 3.85 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ = 170.…”

“…151–152 °C (lit. [ 21 ] m.p. 150–152 °C); 1 H NMR (400 MHz, CDCl 3 ): δ 9.14 (br s, 1H), 7.82 (s, 1H), 7.68 (d, J = 7.6 Hz, 1H), 7.41–7.37 (m, 1H), 7.27–7.19 (m, 3H), 6.98 (dd, J = 8.4, 2.4Hz, 1H), 6.93 (d, J = 7.6 Hz, 1H), 6.89–6.86 (m, 1H), 3.85 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ = 170.7, 159.6, 141.8, 137.3, 136.1, 129.9, 129.7, 127.8, 123.2, 121.8, 121.7, 121.6, 115.6, 114.2, 110.4, 55.3; HRMS (ESI) m/z calcd.…”

“…178–181 °C (lit. [ 21 ] m.p. 178–181 °C); 1 H NMR (400 MHz, CDCl 3 ): δ 8.50 (br s, 1H), 7.75 (s, 1H), 7.62–7.57 (m, 3H), 7.46–7.44 (m, 2H), 7.25–7.21 (m, 1H), 6.92–6.87 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ = 170.4, 141.9, 135.8, 135.5, 133.2, 130.6, 130.2, 128.9, 128.1, 122.9, 121.9, 121.3, 110.5; HRMS (ESI) m/z calcd.…”

Application of SBA-Pr-SO3H in the synthesis of benzoxazole derivatives

“…The TEM image ( Figure 4b) represents the parallel channels that were not collapsed during two step reactions. In general, organic functionalization did not alter the long-range mesoporous arrangement [25,26]. …”

Knoevenagel condensation of isatins with malononitrile/ethyl cyanoacetate in the presence of sulfonic acid functionalized silica (SBA-Pr-SO3H) as a new nano-reactor

“…Here, in continuation of our studies, on the application of heterogeneous solid catalysts to organic synthesis [26][27][28][29][30] we report our results on the condensation of isatin with malononitrile or ethyl cyanoacetate in the presence of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) as a new nano-reactor.…”