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Synlett 2014; 25(08): 1127-1131
DOI: 10.1055/s-0033-1340986
DOI: 10.1055/s-0033-1340986
letter
Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds
Weitere Informationen
Publikationsverlauf
Received: 22. Dezember 2013
Accepted after revision: 19. Februar 2014
Publikationsdatum:
18. März 2014 (online)
Abstract
Selective hydration of nitriles to primary amides as well the base-catalyzed synthesis of 2-substituted 4(1H)-quinazolinones via reaction of 2-aminobenzonitrile with carbonyl compounds using macroporous Amberlyst A26 OH in H2O–EtOH is described. The latter reaction proceeds via tandem hydration of 2-aminobenzonitrile, condensation of the in situ generated 2-aminobenzamide with carbonyl compounds, and cyclization of the imine intermediate to give the quinazolinone derivatives.
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References and Notes
- 1a Sartori G, Maggi R. Chem. Rev. 2010; 113: PR1
- 1b Jafari AA, Amini S, Tamaddon F. J. Appl. Polym. Sci. 2012; 125: 1339
- 1c Zolfigol MA. Tetrahedron 2001; 57: 9509
MissingFormLabel
- 1d Zolfigol MA, Salehi P, Shiri M, Faal Rastegar T, Ghaderi A. J. Iran. Chem. Soc. 2008; 5: 490
- 2a Marigo M, Bertelsen S, Landa A, Jørgensen KA. J. Am. Chem. Soc. 2006; 128: 5475
- 2b Sheldon RA. Wallau M, Arends IW. C. E, Schuchardt U. Acc. Chem. Res. 1998; 31: 485
- 2c Lempers HE. B, Sheldon RA. J. Catal. 1998; 175: 62
- 3a Sharma M, Pandey S, Chauhan K, Sharma D, Kumar B, Chauhan PM. S. J. Org. Chem. 2012; 77: 929
- 3b Bozell JJ, Petersen GR. Green Chem. 2010; 12: 539
- 4a Hattori H. Chem. Rev. 1995; 95: 537
- 4b Tamaddon F, Tayefi M, Hosseini E, Zare E. J. Mol. Catal. A: Chem. 2013; 366: 36
- 5a Tamaddon F, Nasiri A, Farokhi S. Catal. Commun. 2011; 12: 1477
- 5b Tamaddon F, Khoobi M, Keshavarz E. Tetrahedron Lett. 2007; 48: 3643
- 5c Tamaddon F, Sabeti MR, Jafari AA, Tirgir F, Keshavarz E. J. Mol. Catal. A: Chem. 2011; 351: 41
- 5d Tamaddon F, Tavakoli F. J. Mol. Catal. A: Chem. 2011; 337: 52
- 5e Tamaddon F, Kargar-Shooroki H, Jafari AA. J. Mol. Catal. A: Chem. 2013; 368-369: 66
- 5f Tamaddon F, Moradi S. J. Mol. Catal. A: Chem. 2013; 370: 117
- 6a Tamaddon F, Moazeni Bistgani J. Synlett 2011; 2947
- 6b Tamaddon F, Farahi M. Synlett 2012; 23: 1379
- 6c Tamaddon F, Amrollahi MA, Sharafat L. Tetrahedron Lett. 2005; 46: 7841
- 6d Tamaddon F, Razmi Z, Jafari AA. Tetrahedron Lett. 2010; 51: 1187
- 6e Tamaddon F, Razmi Z. Synth. Commun. 2011; 41: 485
- 6f Tamaddon F, Amirpoor F. Synlett 2013; 24: 1791
- 7 Mukhopadhyay C, Kumar Tapaswi P. Catal. Commun. 2008; 9: 2392
- 8 Greluk M, Hubicki Z. Desalination 2011; 278: 219
- 9 Singh AK, Rita P. Microchem. J. 1991; 43: 112
- 10 http://www.sigmaaldrich.com/catalog/search/ProductDetail /ALDRICH/542571.
- 11 Ilgen O, Akin AN, Boz N. Turk. J. Chem. 2009; 33: 289
- 12 Vicente G, Coteron A, Martinez M, Aracil J. Ind. Crop. Prod. 1998; 8: 29
- 13 Girolamo MD, Marchionna M. J. Mol. Catal. A: Chem. 2001; 177: 33
- 14 Girolamo M, Lami M, Marchionna M, Sanfilippo D, Andreoni M, Maria A, Galletti R, Sbrana G. Catal. Lett. 1996; 38: 127
- 15 Serra-Holm V, Salmi T, Multamäki J, Reinik J, Mäki-Arvela P, Sjöholm R, Lindfors LP. Appl. Catal., A 2000; 198: 207
- 16a Chinigo GM, Paige M, Grindrod S, Hamel E, Dakshanamurthy S, Chruszcz M, Minor W, Brown ML. J. Med. Chem. 2008; 51: 4620
- 16b Connolly DJ, Cusack D, OSullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
- 16c Abbas SE, Awdallah FM, Ibrahim NA, Said EG, Kamel GM. Eur. J. Med. Chem. 2012; 53: 141
- 17a Suresha GP, Suhas R, Kapfo W, Gowda DC. Eur. J. Med. Chem. 2011; 46: 2530
- 17b Pal M. Synlett 2009; 2896
- 18a Abdel-Jalil RJ, Voelter W, Saeed M. Tetrahedron Lett. 2004; 45: 3475
- 18b Gao J, He L.-N, Miao C.-X, Chanfreau S. Tetrahedron 2010; 66: 4063
- 18c Gao L, Ji H, Rong L, Tang D, Zha Y, Shi Y, Tu S. J. Hetrocycl. Chem. 2011; 48: 957
- 19a Hazarkhani H, Karimi B. Tetrahedron 2003; 59: 4757
- 19b Salehi P, Dabiri M, Zolfigol MA, Baghbanzadeh M. Tetrahedron Lett. 2005; 46: 7051
- 19c Yavari I, Beheshti S. J. Iran. Chem. Soc. 2011; 8: 1030
- 20a Mizuno T, Ishino Y. Tetrahedron 2002; 58: 3155
- 20b Rostami A, Tavakoli A. Chin. Chem. Lett. 2011; 22: 1317
- 20c Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W. Tetrahedron Lett. 2008; 49: 3814
- 20d Shi D, Rong L, Wang J, Zhuang Q, Wang X, Hu H. Tetrahedron Lett. 2003; 44: 3199
- 20e Zhang L, Li J, Yang X, Shi D, Chen J. Acta Crystallogr., Sect. E: Struct. Rep. Online 2008; 64: 450; part 2
- 20f Zhang LJ, Yu JL, Wang WL, Li H, Xu DD, Bi YD, Liu FD. Tetrahedron Lett. 2014; 55: 710
- 20g Kidwai MP. Indian J. Chem., Sect. B.: Org. Chem. Incl. Med. Chem. 2008; 47: 1876
- 21a Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
- 21b Pattabiraman VR, Bode JW. Nature (London) 2011; 480: 471
- 21c Mansour lakouraj M, Bahrami K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999; 38: 974
- 21d Gadge ST, Bahange BM. Synlett 2014; 25: 85
- 21e Subramanian T, Pitchumani K. Catal. Commun. 2012; 29: 109
- 22a Van Dorsser W, Barris D, Cordi A, Roba J. Arch. Int. Pharmacodyn. Ther. 1983; 266: 239
- 22b Pevarello P, Bonsignori A, Dostert P, Heidempergher F, Pinciroli V, Colombo M, McArthur RA, Salvati P, Post C, Fariello RG, Varasi M. J. Med. Chem. 1998; 41: 579
- 22c Ghidini E, Delcanale M, De Fanti R, Rizzi A, Mazzuferi M, Rodi D, Simonato M, Lipreri M, Bassani F, Battipaglia L, Bergamaschi M, Villetti G. Bioorg. Med. Chem. 2006; 14: 3263
- 23 General Procedure for the Synthesis of 2-Substituted 2,3-dihydro-4(1H)-quinazolinones Amberlyst A26 OH (0.11 g) was added to a solution of 2-aminobenzonitrile (1 mmol) and the requisite benzaldehyde (1 mmol) in EtOH–H2O (0.5 mL). The reaction mixture was stirred at 50–60 °C for the specified period of time as indicated in Table 2, and the progress of the reaction was followed by TLC. After the completion reaction, the mixture was diluted with hot EtOH and filtered to remove the catalyst. The desired products were isolated by addition of H2O and filtration of the precipitate. To check the regenerability of Amberlyst A26 OH from the model reaction of 2-aminobenzonitrile with benzaldehyde, Amberlyst was removed after reaction completion by dispersing the reaction mixture in warm EtOH or EtOAc and filtering the reaction mixture. To remove impurities and regeneration of the filtered resin, it was washed with EtOAc, distilled H2O, and 0.1 M NaOH and dried at r.t.
- 24 General Procedure for Synthesis of Primary Amides Amberlyst A26 OH (0.11 g) was added to a suspension of the nitrile (1 mmol) in EtOH–H2O (0.5 mL). The reaction mixture was stirred at 50–60 °C, and the progress of the reaction was followed by TLC. After the completion of reaction, the mixture was diluted with acetone or EtOAc and filtered to remove the catalyst. The desired products were isolated by evaporation of the EtOAc or addition of H2O and filtration of the precipitate. Selected Spectroanalytical Data for Products 2-(Phenyl)-2,3-dihydro-4(1H)-quinazolinone (Table 3, Entry 1) White solid; mp 219–222 °C; yield: 93%. FTIR (KBr): νmax = 3302 (NH), 3055 (CH), 1655 (C=O) cm–1. 1H NMR (500 MHz, CDCl3): δ = 4.40 (br s, 1 H, NH), 5.85 (br s, 1 H, CH), 6.60–6.70 (m, 2 H, Harom), 6.95–7.10 (m, 1 H, Harom), 7.20–7.38 (m, 4 H, Harom), 7.58–7.78 (m, 2 H, Harom), and 7.94 (d, J = 10 Hz, 1 H, NH) ppm. 13C NMR (125 MHz, CDCl3): δ = 72.5, 119.5, 119.8, 122.6, 132.1, 132.5, 132.6, 132.8, 138.5, 145.8, 152.9, 169.6 ppm. 2-(Pyridin-3′-yl)-2,3-dihydroquinazolin-4(1H)-one (Table 3, Entry 11) White solid; mp 189–192 °C (lit.3a 190–192 °C); yield: 92%. FTIR (KBr): νmax = 3310 (NH), 3065 (CH), 1660 (C=O), 1612 cm–1. 1H NMR (500 MHz, CDCl3): δ = 5.90 (s, 1 H, NH), 6.65 (d, J = 8.0 Hz, 1 H, CH), 6.81 (t, J = 7.9 Hz, 1 H, Harom), 7.23–7.38 (m, 3 H, Harom), 7.77 (dd, J 1 = 7.8 Hz, J 2 = 1.5 Hz, 1 H), 7.93–7.99 (m, 1 H, NH), 8.53 (dd, J 1 = 4.8 Hz, J 2 = 1.5 Hz, 1 H), 8.6 (s, 1 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 69.5, 117.5, 118.7, 119.8, 122.6, 128.5, 131.6, 138.2, 139.5, 140.8, 151.5, 151.9, 153.9, 169.6 ppm. 1′H-Spiro[cyclohexane-1,2′-quinazolin]-4′(3′H)-one White solid; mp 225–227 °C; yield: 90%. FTIR (KBr): νmax = 3305 (NH), 3065 (CH), 1665 (C=O) cm–1. 1H NMR (500 MHz, CDCl3): δ = 1.48–1.68 (m, 6 H), 1.85 (br s, 4 H), 4.40 (br s, 1 H, NH), 6.43 (s, 1 H, NH), 6.66 (d, J = 5.2 Hz, 1 H), 6.82 (t, J = 5.2 Hz, 1 H), 7.28–7.35 (m, 1 H), 7.87 (dd, J 1 = 7.5 Hz, J 2 = 1.0 Hz, 1 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 24.0, 26.8, 39.7, 70.5, 117.0, 119.0, 120.8, 130.4, 136.2, 148, 167.0 ppm. Benzamide (Table 4, Entry 3) White crystals; mp 129–131 °C (lit.25a 129 °C); yield: 91%. FTIR (neat): νmax = 3369, 3171, 1657 cm–1. 1H NMR (250 MHz, CDCl3): δ = 6.15 (s, NH2, 2 H), 7.46 (t, J = 6.0 Hz, 1 H), 7.55 (t, J = 6.0 Hz, 2 H), 7.83 (d, J = 6.0 Hz, 2 H, Ph) ppm. Nicotinamide (Table 4, Entry 6) White crystals; mp 129–131 °C (lit.25b 131 °C); yield: 94%. FTIR (neat): νmax = 3275, 3410, 1601 cm–1; 1H NMR (250 MHz, DMSO-d 6): δ = 7.47 (t, J = 5.0 Hz, 1H), 7.59 (s, 2 H, NH2), 8.18 (d, J = 5.0 Hz, 1 H), 8.67 (d, J = 5.0 Hz, 2 H, Ph), 9.00 (s, 1 H) ppm. 13C NMR (62.5 MHz, DMSO-d 6): δ = 123.9, 130.1, 135.6, 149.1, 152.3, 166.9 ppm.