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Synlett 2015; 26(04): 525-530
DOI: 10.1055/s-0034-1379881
DOI: 10.1055/s-0034-1379881
letter
Cocamidopropyl Betaine Catalyzed Benzoin Condensation and Pseudo-Four-Component Reaction of the in Situ Formed Benzoin in Water
Weitere Informationen
Publikationsverlauf
Received: 26. Oktober 2014
Accepted after revision: 15. November 2014
Publikationsdatum:
13. Januar 2015 (online)
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.
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References and Notes
- 1a Li CJ. Chem. Rev. 1999; 93: 2023
- 1b Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
- 1c Li CJ. Chem. Rev. 2005; 105: 3095
- 1d Tamaddon F, Razmi Z. Synth. Commun. 2011; 41: 485
- 1e Tamaddon F, Tayefi M, Hosseini E, Zare E. J. Mol. Catal. A: Chem. 2013; 366: 36
- 1f Firouzabadi H, Iranpoor N, Gholinejad M. J. Organomet. Chem. 2010; 695: 2093
- 1g Hasaninejad A, Shekouhy M, Mohammadizadeh MR, Zare A. RSC Adv. 2012; 2: 6174
- 1h Tamaddon F, Pouramini F. Synlett 2014; 25: 1127
- 2a Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
- 2b Dwars T, Paetzold E, Oehme G. Angew. Chem. Int. Ed. 2005; 44: 7174
- 2c Shiri M, Zolfigol MA. Tetrahedron 2009; 65: 587
- 2d Merchán Arenas DR, Martínez Bonilla CA, Kouznetsov VV. Org. Biomol. Chem. 2013; 11: 3655
- 2e Manabe K, Mori Y, Wakabayashi T, Nagayama S, Kobayashi S. J. Am. Chem. Soc. 2000; 122: 7202
- 3a Chu Z, Dreiss AC, Feng Y. Chem. Soc. Rev. 2013; 42: 7174
- 3b Acharya DP, Kunieda H. Adv. Colloid Interfac. 2006; 401: 123
- 3c Yang J. Curr. Opin. Colloid Interfac. Sci. 2002; 7: 276
- 3d Dreiss AC. Soft Matter 2007; 3: 956
- 3e Davies TS, Ketner AM, Raghavan SR. J. Am. Chem. Soc. 2006; 18: 6669
- 3f Ketner AM, Kumar R, Davies TS, Elder PW, Raghavan SR. J. Am. Chem. Soc. 2007; 129: 1553
- 3g Zhang Y, Han Y, Chu Z, He S, Zhang J, Feng Y. J. Colloid Interfac. Sci. 2013; 394: 319
- 4a Quan H, Zhang X, Lu X, Huang Z. Centr. Eur. J. Chem. 2012; 10: 1624
- 4b Candau SJ, Oda R. Colloids Surf. A. 2001; 5: 183
- 4c Kumar R, Kalur GC, Ziserman L, Danino D, Raghavan SR. Langmuir 2007; 23: 12849
- 4d Maeda H, Yamamoto A, Souda M. J. Phys. Chem. B 2001; 105: 5411
- 4e Sarmiento-Gomez E, Lopez-Diaz D, Castillo R. J. Phys. Chem. B 2010; 114: 12193
- 4f Tamaddon F, Alizadeh M. Tetrahedron Lett. 2014; 55: 3588
- 5a Benzoin condensation. In Comprehensive Organic Name Reactions and Reagents. John Wiley; New York: 2010
- 5b Pan F, Chen TM, Cao JJ, Zou JP, Zhang W. Tetrahedron Lett. 2012; 53: 2508
- 5c Li B, Wang J, Fu J, Wang J, Zou C. Catal. Commun. 2008; 9: 2000
- 6a Mousavi M, Seyfi H. Org. Chem. J. 2011; 1: 17
- 6b Bhattacharya A, Purohit VC, Beller NR. J. Chem. Educ. 2004; 81: 1020
- 7 Kiasat AR, Badri R, Sayyahi S. Bull. Korean Chem. Soc. 2009; 30: 1164
- 8a Kochiusa S, Paetzolda M, Scholz A, Merkens H, Vogel A, Ansorge-Schumacher M, Hollmann F, Schrader J, Holtmann D. J. Mol. Catal. B: Enzym. 2014; 103: 61
- 8b Iwamoto K, Kimura H, Oike M, Sato M. Org. Biomol. Chem. 2008; 6: 912
- 8c Iwamoto K, Hamaya M, Hashimoto N, Kimura H, Suzuki Y, Sato M. Tetrahedron Lett. 2006; 47: 7175
- 8d Demir AS, Pohl M, Janzen E, Müller M. J. Chem. Soc., Perkin Trans. 1 2001; 633
- 9a O’Toole SE, Connon SJ. Org. Biomol. Chem. 2009; 7: 3584
- 9b Soeta T, Tabatake Y, Inomata K, Ukaji Y. Tetrahedron 2012; 68: 894
- 9c Rafiński Z, Kozakiewicz A, Rafińska K. Tetrahedron 2014; 70: 5739
- 9d Jin MY, Kim SM, Han H, Ryu DH, Yang JW. Org. Lett. 2011; 13: 880
- 10a Iwamoto K.-I, Hamaya M, Hashimoto N, Kimura H, Suzuki Y, Sato M. Tetrahedron Lett. 2006; 47: 7175
- 10b Estager J, Lévêque J.-M, Turgis R, Draye M. J. Mol. Catal. A: Chem. 2006; 256: 261
- 10c Aupoix A, Pégot B, Vo-Thanh G. Tetrahedron 2010; 66: 1352
- 10d Xu L.-W, Gao Y, Yin J.-J, Lia L, Xia C.-G. Tetrahedron Lett. 2005; 46: 5317
- 10e Estager J, Lévêque J.-M, Turgis R, Draye M. Tetrahedron Lett. 2007; 48: 755
- 10f Emrah Mavis M, Yolacan C, Aydogan F. Tetrahedron Lett. 2010; 51: 4509
- 10g John M, Storey D, Williamson C. Tetrahedron Lett. 2005; 46: 7337
- 11 Shylesh S, Zhou Z, Meng Q, Wagener A, Seifert A, Ernst S, Thiel WR. J. Mol. Catal. A: Chem. 2010; 332: 65
- 12a Adams R, Marvel CS. Org. Synth. 1941; 1: 94
- 12b Lapworth A. J. Chem. Soc., Trans. 1904; 85: 1206
- 13 Tamaddon F, Farahi M. Synlett 2012; 23: 1379
- 14a Jiang B, Rajale T, Wever W, Jiang S, Guigen T. Chem. Asian J. 2010; 5: 2318
- 14b Graaff C, Ruijte E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
- 14c Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
- 14d Brauch S, Van Berkela SS, Westermann B. Chem. Soc. Rev. 2013; 42: 4948
- 14e Slobbe P, Ruijter E, Orru RV. A. Med. Chem. Commun. 2012; 3: 1189
- 14f Eckert H. Molecules 2012; 17: 1074
- 14g Zhu J, Bienaymé H. Multicomponent Reactions 2005
- 14h Weber L. Curr. Med. Chem. 2002; 9: 2085
- 14i Rahman M, Sarkar A, Ghosh M, Majee A, Hajra A. Tetrahedron Lett. 2014; 55: 235
- 14j Madabhushi S, Reddy Godala K, Jillella R, Kumar Reddy Mallu K, Chinthala N. Tetrahedron Lett. 2014; 55: 514
- 14k Akbarzadeh R, Amanpour T, Khavasi HR, Bazgir A. Tetrahedron 2014; 70: 169
- 15a Tamaddon F, Moradi S. J. Mol. Catal. A: Chem. 2013; 370: 117
- 15b Csoüturotuki R, Szatamri I, Fülhop F. Curr. Org. Synth. 2013; 10: 564
- 15c De Benedetto MV, Green ME, Wan S, Park J.-H, Floreancig PE. Org. Lett. 2009; 11: 835
- 15d Kargar M, Hekmatshoar R, Mostashari AJ, Hashemi Z. Catal. Commun. 2011; 15: 123
- 15e Xin X, Wang Y, Kumar S, Liu X, Lin Y, Dong D. Org. Biomol. Chem. 2010; 8: 3078
- 15f Khan MN, Pal S, Karamthulla S, Choudhury LH. RSC Adv. 2014; 4: 3732
- 16a Gu Y. Green Chem. 2012; 14: 2091
- 16b Pirrung MC, Das Sarma K. J. Am. Chem. Soc. 2004; 126: 444
- 16c Gawande MB, Bonifácio VD. B, Luque R, Brancoa PS, Varma RS. Chem. Soc. Rev. 2013; 42: 5522
- 16d Tamaddon F, Razmi Z, Jafari AA. Tetrahedron Lett. 2010; 51: 1187
- 16e Ghosh PP, Mukherjee P, Das AR. RSC Adv. 2013; 3: 8220
- 16f Jafari AA, Moradgholi F, Tamaddon F. Eur. J. Org. Chem. 2009; 1249
- 16g Jafari AA, Moradgholi F, Tamaddon F. J. Iran. Chem. Soc. 2009; 6: 588
- 16h Tamaddon F, Bistgani JM. Synlett 2011; 2947
- 16i Jafari AA, Amini S, Tamaddon F. J. Appl. Polym. Sci. 2011; 125: 1339
- 16j Khalili B, Jajarmi P, Eftekhari-Sis B, Hashemi MM. J. Org. Chem. 2008; 73: 2090
- 16k Pagadala R, Maddila S, Dasireddy VD. B. C, Jonnalagadda SB. Catal. Commun. 2014; 45: 148
- 16l Candeias NR, Paterna R, Cal PM. S. D, Góis PM. P. J. Chem. Educ. 2012; 89: 799
- 16m Gan S.-F, Wan J.-P, Pan Y.-J, Sun C.-R. Synlett 2010; 6: 973
- 16n Hasaninejad A, Shekouhy M, Mohammadi Zadeh MR, Zare A. RSC Adv. 2012; 2: 6174
- 16o Rajarathinam B, Vasuki G. Org. Lett. 2012; 14: 5204
- 17a Meng F, Xu J. Tetrahedron 2013; 69: 4944
- 17b Teimouri MB, Akbari-Moghaddam P. Tetrahedron 2011; 67: 5928
- 17c Ghahremanzadeh R, Amanpour T, Bazgir A. Tetrahedron Lett. 2010; 51: 4202
- 17d Shaabani A, Hajishaabanha F, Mahyari M, Mofakham H, Weng NgS. Tetrahedron 2011; 67: 8360
- 17e Muthusaravanan S, Perumal S, Almansour AI. Tetrahedron Lett. 2012; 53: 1144
- 17f Karimi AR, Behzadi F, Faghihi K. Mol. Divers. 2009; 13: 379
- 17g Shafiee M, Khosropour AR, Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V. Tetrahedron Lett. 2012; 53: 3086
- 17h Mofakham H, Shaabani A, Mousavifaraz S, Hajishaabanha F, Shaabani S. Mol. Divers. 2012; 16: 351
- 17i Nair V, Varghese V, Babu BP, Sinu CR, Suresh E. Org. Biomol. Chem. 2010; 8: 761
- 17j Ghahremanzadeh R, Imani Shakibaei G, Ahadi S, Bazgir A. J. Comb. Chem. 2010; 12: 191
- 18a Estévez V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2010; 39: 4402
- 18b Estévez V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2014; 43: 4633
- 18c Fan H, Peng J, Hamann MT, Hu J.-F. Chem. Rev. 2008; 108: 264
- 18d Yasui E, Wada M, Takamura N. Tetrahedron Lett. 2009; 50: 4762
- 18e Bellina F, Rossi R. Tetrahedron 2006; 62: 7213
- 18f Denny WA, Rewcastle GW, Baguley BC. J. Med. Chem. 1990; 33: 814
- 18g Thirumalairajan S, Pearce BM, Thompson A. Chem. Commun. 2010; 46: 1797
- 18h Bandyopadhyay D, Mukherjee S, Granados JC, Short Bimal JD, Banik K. Eur. J. Med. Chem. 2012; 50: 209
- 18i Anary-Abbasinejad M, Charkhati K, Anary-Ardakani H. Synlett 2009; 1115
- 18j Bhunia N, Das B. Synthesis 2013; 45: 1045
- 18k Berlin A, Vercelli B, Zotti G. Polym. Rev. 2008; 48: 493
- 19a Young IS, Thornton PD, Thompson A. Nat. Prod. Rep. 2010; 27: 1801
- 19b Lehninger CM, Nelson AL, Lehninger DR. Principles of Biochemistry. Worth Publishers; New York: 2000
- 20a Li BL, Li PH, Fang XN, Li CX, Sun JL, Mo LP, Zhang ZH. Tetrahedron 2013; 69: 7011
- 20b Estévez V, Villacampa M, Menéndez JC. Chem. Commun. 2013; 49: 591
- 20c Suresh R, Muthusubramanian S, Nagaraj M, Manickam G. Tetrahedron Lett. 2013; 54: 1779
- 20d Atar AB, Jeong YT. Tetrahedron Lett. 2013; 54: 5624
- 20e Rajeshwar Reddy G, Ram Reddy T, Joseph SC, Sateesh Reddya K, Pal M. RSC Adv. 2012; 2: 3387
- 20f Ghabraie E, Balalaie S, Bararjanian M, Bijanzade HR, Rominger F. Tetrahedron 2011; 67: 5415
- 20g Khan AT, Lal M, Bagdi PR, Basha RS, Saravanan P, Patra S. Tetrahedron Lett. 2012; 53: 4145
- 20h Attanasi OA, Favi G, Mantellini F, Moscatelli G, Santeusanio S. J. Org. Chem. 2011; 76: 2860
- 20i Sukhendu M, Srijit B, Umasish J. J. Org. Chem. 2010; 75: 1674
- 20j Xu P, Huang K, Liu Z, Zhou M, Zeng W. Tetrahedron Lett. 2013; 54: 2929
- 20k Zhang L, Wang X, Li S, Wu J. Tetrahedron 2013; 69: 3805
- 20l Alizadeh A, Babaki M, Zohreh N. Tetrahedron 2009; 65: 1704
- 20m Procopiou PA, Draper CD, Hutson JL, Inglis GG. A, Ross BC, Watson NS. J. J. Med. Chem. 1993; 36: 3658
- 21a Tamaddon F, Farahi M, Karami B. J. Mol. Catal. A: Chem. 2012; 356: 85
- 21b Tamaddon F, Amirpoor F. Synlett 2013; 24: 1791
- 22a Li W, Han Y.-C, Zhang J.-L, Wang B.-G. Colloid J. 2005; 67: 159
- 22b Rafati AA, Maleki H. J. Mol. Liq. 2007; 135: 128
- 23 Bhat SI, Trivedi DR. Tetrahedron Lett. 2013; 54: 5577
- 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, HAr), 7.25 (d, J = 10.8 Hz, 4 H, HAr), 7.01 (d, J = 7.2 Hz, 2 H, HAr), 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, HAr), 7.25 (d, J = 8.4 Hz, 2 H, HAr), 7.86 (t, J = 7.2 Hz, 4 H, HAr), 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, HAr), 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.