A Convenient Method for the Preparation of 1,5‐Diaryl‐3‐(arylamino)‐1H‐pyrrol‐2(5H)‐ones

Abstract

A simple and eco-friendly method for the preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones via the cyclo-condensation reaction of aldehydes, amines and ethyl pyruvate in the presence of silica supported ferric chloride (SiO 2 -FeCl 3 ) as reusable heterogeneous catalyst is described. The present methodology offers several advantages such as excellent yields, simple procedure and short reaction times.

Schiff base Mo(vi) complexes grafted on Merrifield resin as recyclable and efficient catalysts for the synthesis of pyrrole-2-ones

“…197–198 °C (lit. : 17 195–197 °C); 1 H NMR (500 MHz, CDCl 3 ) δ 7.40–7.32 (m, 2H), 7.31–7.16 (m, 6H), 7.06–7.00 (m, 2H), 6.88–6.77 (m, 4H), 6.47 (s, 1H), 5.93 (d, J = 2.6 Hz, 1H), 5.57 (d, J = 2.6 Hz, 1H), 3.77 (s, 3H), 3.74 (s, 3H). 13 C NMR (125 MHz, CDCl 3 ) δ 167.19, 156.96, 154.41, 137.67, 134.86, 132.99, 130.28, 128.89, 128.11, 126.93, 123.78, 118.46, 114.69, 114.15, 106.18, 64.76, 55.60, 55.34.…”

“…210–212 °C (lit. : 17 214–216 °C); 1 H NMR (500 MHz, CDCl 3 ) δ 7.56–7.46 (m, 2H), 7.36–7.21 (m, 8H), 7.21–7.15 (m, 2H), 7.03–6.96 (m, 2H), 6.64 (s, 1H), 6.05 (d, J = 2.6 Hz, 1H), 5.64 (d, J = 2.6 Hz, 1H); 13 C NMR (125 MHz, CDCl 3 ) δ 167.00, 139.72, 136.82, 135.72, 131.76, 130.25, 129.37, 129.21, 129.05, 128.48, 126.64, 126.20, 122.49, 117.89, 108.62, 64.21.…”

“…In the current research methods of synthesizing pyrrole-2-ones, different catalysts have been developed and used, such as organic catalysts: fluoroimine thiocarbonate, 14 thioureas and phosphoric acids, 15 and benzoic acid. 16 Besides, inorganic catalysts including silica supported ferric chloride (SiO 2 –FeCl 3 ), 17 polyoxometalate immobilized on MOF-5, 18 magnetic CoFe 2 O 4 nanoparticles, 19 NiFe 2 O 4 nanoparticles, 20 acidic ionic liquid triethylammonium hydrogen sulfate ([Et 3 NH][HSO 4 ]), 21 and Lewis acid Yb(OTF) 3 22,23 have also been studied.…”

Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using aluminum methanesulfonate as a reusable catalyst

“…Very recently, Dabiri and Salehi first reported that 2,3-dihydroquinazolin-4(1H)-ones could be synthesized from a novel one-pot three components condensation of isatoic anhydride, an aromatic aldehyde, and a primary amine or ammonium salts [18,19]. Since then, some other catalysts such as p-TsOH [20], acetic acid [21], Zn(PFO) 2 [22], Ga(OTf) 3 [23], ionic liquid [24,25], montmorillonite K-10 [26,27], Al(H 2 PO 4 ) 3 [28], I 2 [29,30], amberlyst-15 [31], silica sulfuric acid [32], silica-bonded S-sulfonic acid [33], Al/Al 2 O 3 and Fe 3 O 4 nanoparticles [34,35], copolymer-PTSA [36], MCM-41-SO 3 H [37], SiO 2 -FeCl 3 [38] and silica-bonded N-propylsulfamic acid [39] have also been reported. However, these methodologies suffer from at least one of the following disadvantages: long reaction time, high temperature, and costly reagents.…”

Synthesis of novel pyrrole derivatives from the multicomponent reaction using the new N‐sulfonic acid modified poly (styrene‐diethylenetriamine) as a solid acid catalyst

“…1 H NMR (400.13 MHz, CDCl 3 ): δ H : 6.32 (1H, d, 3 J HH = 2.8 Hz, CH), 6.48 (1H, d, 3 J HH = 2.8 Hz, CH), 6.70 (1H, s, NH), 6.99 (1H, t, 3 J HH = 7.6 Hz, CH Ar ), 7.09-7.14 (2H, m, CH Ar ), 7.21-7.23 (1H, m, CH Ar ), 7.28-7.35 (4H, m, CH Ar ), 7.37-7.47 (2H, m, 13 C NMR (100.6 13 C NMR (100.6 MHz, CDCl 3 ): δ C : 60.1 (CHN), 106.3, 116.7, 120.5, 121.3, 124.7, 127.0, 127.7, 129.0, 129.1, 129.4, 129.8, 132.5, 133.0, 134.7, 137.1, 141.1, 167.3 (C=O). MS: m/z [%]: 360 [100], 362 [62], 297 [75], 268 [100], 240 [100], 229 [100], 204[29], 92[17], 77[15] 1. H NMR (400.13 MHz, CDCl 3 ): δ H : 4.00 (3H, s, OCH 3 ), 6.16 (1H, d, 3 J HH = 2.8 Hz, CH), 6.26 (1H,d, 3 J HH = 2.8 Hz, CH), 6.65 (1H, s, NH), 6.81 (1H, t, 3 J 2.5.16 | 5-(2-Metoxyphenyl)-1-(p-tolyl)-3-(ptolylamino)-1,5-dihydro-2H-pyrrol-2-one (4p) White cream powder, IR (KBr): ν max 3328 (N-H), 3027 (C SP 2 -H), 2920 (C SP 3 -H), 1669 (C=O), 1535 (C=C) cm 1 H NMR (400.13 MHz, CDCl 3 ): δ H : 2.29 (3H, s, CH 3 ), 2.31 (3H, s, CH 3 ), 5.62 (1H, d, 3 J HH = 2.4 Hz, CH), 5.98 (1H, d, 3 J HH = 2.8 Hz, CH), 7.00 (2H, t, 3 J HH = 7.2 Hz, CH Ar ), 7.10-7.14 (5H, m, CH Ar + NH), 7.15-7.16 (2H, m, CH Ar ), 7.25-7.28 (2H, m, CH Ar ), 7.36 (2H, dd, 3 J HH = 6.4 Hz, 4 J HH = 2.0 Hz, CH Ar ).…”