Cocamidopropyl Betaine Catalyzed Benzoin Condensation and Pseudo-Four-Component Reaction of the in Situ Formed Benzoin in Water

Abstract

An improved synthesis of benzoins, as key synthetic building blocks, and substituted pyrroles in micelle medium using a very small amount of cocamidopropyl betaine in water is described. In this one-pot strategy, benzoin condensation of aldehydes and further pseudo-four-component reaction of the in situ formed benzoin with 1,3-dicarbonyls, and ammonium acetate gave excellent yields of the desired pyrrole products.

Key words

pseudo-four-component reaction - water - pyrrole - CAPB - zwitterionic surfactant - benzoin condensation - worm-like micelles

• References and Notes

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• 24 General Procedure for the Benzoin Condensation: Aldehyde (2 mmol) and sodium cyanide (20 mol%) were added to a stirred solution of H₂O–EtOH (80:20) and CAPB (0.3 mol%) and the mixture was stirred for the time stated at 55–65 °C. After completion of condensation [TLC monitoring with hexane–EtOAc (8:2)], the precipitated benzoin was washed with H₂O and filtered.
• 25 General Procedure for Tandem Benzoin Condensation and pMCR Synthesis of Tetrasubstituted Pyrroles: After completion of the reaction of aldehyde (5 mmol), sodium cyanide (20 mol%), and CAPB (0.3 mol%) in H₂O–EtOH (80:20; TLC monitoring), the requisite 1,3-dicarbonyl compound (5 mmol) and ammonium acetate (6 mmol) were added to the stirred reaction mixture at 55–65 °C. After completion of the second step, cold H₂O (40 mL) was added and the pyrrole product was isolated by filtration without need for further purification. Spectroscopic data of representative compounds follows. 2-Hydroxy-1,2-bis(4-methylphenyl)ethanone (2d): white powder; mp 80–81 °C. FT-IR (KBr): 3446 (OH stretching), 2920, 1609 (C=O), 1574, 1511, 1418, 1284, 1183, 1117, 1083, 971, 806, 754, 724, 667 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆): δ = 7.85 (d, J = 6.8 Hz, 2 H, H_Ar), 7.25 (d, J = 10.8 Hz, 4 H, H_Ar), 7.01 (d, J = 7.2 Hz, 2 H, H_Ar), 6.10 (s, 1 H, CH), 5.80 (d, 1 H, OH), 2.30 (s, 3 H, Me), 2.21 (s, 3 H, Me). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 197.0, 141.55, 136.0, 135.96, 129.9, 128.1, 127.4, 124.8, 75.8, 21.7, 21.3. 2-Hydroxy-1,2-bis(4-methoxyphenyl)ethanone (2e): white powder; mp 118–119 °C. FT-IR (KBr): 3464 (OH stretching), 1666 (C=O), 1597, 1514, 1468, 1386, 1313, 1265, 1240, 1170, 1116, 1023, 979, 832, 794, 733 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆): δ = 7.91 (d, J = 8.4 Hz, 2 H, H_Ar), 7.25 (d, J = 8.4 Hz, 2 H, H_Ar), 7.86 (t, J = 7.2 Hz, 4 H, H_Ar), 5.87 (d, J = 5.2 Hz, 1 H), 4.60 (d, J = 5.2 Hz, 1 H, OH), 3.83 (s, 3 H, Me), 3.76 (s, 3 H, Me). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 195.7, 162.8, 158.2, 131.0, 130.8, 128.5, 120.3, 113.5, 74.4. Ethyl 2-Methyl-4,5-diphenyl-1H-pyrrole-3-carboxylate (5b): yellow solid; mp 207–209 °C. FT-IR (KBr): 3306 (NH stretching), 1673 (C=O), 1598, 1442, 1480, 1181, 1098, 758, 693 cm^–1.¹H NMR (400 MHz, DMSO-d ₆): δ = 11.56 (br s, 1 H, NH), 7.11–7.24 (m, 10 H), 3.91 (q, 2 H, CH₂), 3.34 (s, 3 H, Me), 0.98 (s, 3 H, Me). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 165.1, 137.1, 136.3, 132.7, 131.1, 128.6, 127.9, 127.3, 127.2, 126.5, 123.0, 111.9, 50.8, 14.3, 13.7. 1-[4,5-Bis(4-chlorophenyl)-2-phenyl-1H-pyrrol-3-yl]ethanone (5h): yellow crystals; mp 247–251 °C. FT-IR (KBr): 3302 (NH stretching), 1616, 1595, 1495, 1202, 1094, 1012, 972, 831 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆): δ = 11.85 (s, 1 H, NH), 7.18–7.48 (m, 13 H, H_Ar), 2.21 (s, 3 H, Me). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 193.0, 140.2, 135.1, 134.7, 132.4, 131.97, 131.58, 131.05, 129.3, 128.9, 128.4, 128.3, 126.4, 121.7, 62.0, 13.2.