Microwave-assisted catalyst-free and solvent-free method for the synthesis of quinoxalines

Synthetic Communications

Volumn 39, Issue 20, 2009, Pages 3743-3754

  Zhou, Jian Feng ^a,b   Gong, Gui Xia ^b   Zhi, San Jun ^a   Duan, Xiu Li ^a  

^a HUAIYIN NORMAL UNIVERSITY   (China)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

1,2 diaminobenzene; Benzil; Catalyst free; Microwave irradiation; Quinoxaline; Solvent free

Indexed keywords

1,2 PHENYLENEDIAMINE; QUINOXALINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENVIRONMENTAL PROTECTION; MICROWAVE RADIATION; REACTION TIME;

EID: 70349199742     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902838862     Document Type: Article

References (50)

1. Kappe, C. O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Inter. Ed. 2004, 43, 6250-6284
2. Ding, D. R.; Li, X.; Wang, X.; Du, Y. L.; Shen, J. K. Microwave-assisted rapid and straight-forward synthesis of 2-aryl-4-quinolones from acylated 20-aminoaceto-pheinones. Tetrahderon Lett. 2006, 47, 6997-6999.
3. Loupy, A.; Petti, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. New solvent-free organic synthesis using focused microwaves. Synthesis 1998, 1213-1234
4. Motiwala, H. F.; Kumar, R.; Chakraborti, A. K. Microwave-accelerated solvent-and catalyst-free synthesis of 4-aminoaryl= alkyl-7-chloroquinolines and 2-aminoaryl=alkylbenzothiazoles. Aust. J. Chem. 2007, 60, 369-374
5. Jeselnik, M.; Varma, R. S.; Polanc, S.; Kocevar, M. Catalyst-free reactions under solvent-free conditions: Microwave-assisted synthesis of heterocyclic hydrazones below the melting points of neat reactants. Chem. Commun. (Camb). 2001, 21, 1716-1717
6. Mu, X. J.; Lei, M. Y.; Zou, J. P.; Zhang, W. Microwave-assisted solvent-free and catalyst-free Kabachnik-Fields reactions for a-amino phosphonates. Tetrahedron Lett. 2006, 47, 1125-1127.
7. Sanna, P.; Carta, A.; Loriga, M.; Zanetti, S.; Sechi, L. Synthesis of substituted 2-ethoxycarbonyl-and 2-carboxyquinoxalin-3-ones for evaluation of antimicrobial and anticancer activity. Farmaco 1998, 53, 455-461
8. Hazeldine, S. T.; Polin, L.; Kushner, J.; White, K.; Corbett, T. H.; Biehl, J.; Horwitz, J. P. Synthetic modification of the 2-oxypropionic acid moiety in 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy} propionic acid (XK469), and consequent antitumor effects, part 4. Bioorg. Med. Chem. 2005, 13, 3910-3920.
9. Seitz, L. E.; Suling, W. J.; Reynolds, R. C. Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives. J. Med. Chem. 2002, 45, 5604-5606.
10. Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues. Bioorg. Med. Chem. Lett. 2004, 14, 541-544.
11. Toshima, K.; Takano, R.; Ozawa, T.; Matsumura, S. Molecular design and evaluation of quinoxaline-carbohydrate hybrids as novel and efficient photo-induced GG-selective DNA cleaving agents. Chem. Commun. 2002, 212-213.
12. Monge, A.; Palop, J. A.; Del Castillo, J. C.; Caldero, J. M.; Roca, J.; Romero, G.; Del Rio, J.; Lasheras, B. Novel antagonists of 5-HT3 receptors: Synthesis and biological evaluation of piperazinylquinoxaline derivatives A. J. Med. Chem. 1993, 36, 2745-2750.
13. Rong, F.; Chow, S.; Yan, S.; Larson, G.; Hong, Z.; Wu, J. Structure-activity relationship (SAR) studies of quinoxalines as novel HCV NS5B RNA-dependent RNA polymerase inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 1663-1666.
14. Sonawane, N. D.; Rangnekar, D. W. Synthesis and application of 2-styryl-6,7-dichlorothiazolo(4,5-b)quinoxaline based fluorescent dyes: Part 3. J. Heterocycl. Chem. 2002, 39, 303-308
15. Katoh, A.; Yoshida, T.; Ohkanda, J. Synthesis of quinoxaline deriratives bearing the styryl and phe-nylethynyl groups and application to a fluorescence derivatization reagent. Heterocycles 2000, 52, 911-920.
16. Mizuno, T.; Wei, W. H.; Eller, L. R.; Sessler, J. L. Phenanthroline complexes bearing fused dipyrrolylquinoxaline anion recognition sites: Efficient fluoride anion receptors. J. Am. Chem. Soc. 2002, 124, 1134-1135.
17. Crossley, J. C.; Johnston, L. A. Laterally extended porphyrin systems incorporating a switchable unit. Chem. Commun. 2002, 1122-1123.
18. Dailey, S.; Feast, J. W.; Peace, R. J.; Sage, I. C.; Till, S.; Wood, E. L. Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications. J. Mater. Chem. 2001, 11, 2238-2243.
19. Kim, S. Y.; Park, K. H.; Chung, Y. K. Manganese(IV) dioxide-catalyzed synthesis of quinoxalines under microwave irradiation. Chem. Commun. 2005, 1321-1323.
20. Aparicio, D.; Attanasi, O. A.; Filippone, P.; Ignacio, R.; Lillini, S.; Mantellini, F.; Palacios, F.; de los Santos, J. M. Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1, 3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions. J. Org. Chem. 2006, 71, 5897-5905.
21. Wu, Z.; Ede, N. J. Solid-phase synthesis of quinoxalines on SynPhaseTM lanterns. Tetrahedron Lett. 2001, 42, 8115-8118
22. Singh, S. K.; Gupta, P.; Duggineni, S.; Kundu, B. Solid phase synthesis of quinoxalines. Synlett 2003, 2147-2150.
23. Mao, L.; Sakurai, H.; Hirao, T. Facile synthesis of 2,3-disubstituted quinox-alines by Suzuki-Miyaura coupling. Synthesis 2004, 2535-2539.
24. Zhao, Z.; Wisnoski, D. D.; Wolkenberg, S. E.; Leister, W. H.; Wang, Y.; Lindsley, C. W. General microwave-assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines. Tetrahedron Lett. 2004, 45, 4873-4876
25. Feng, J.; Yang, L.; Meng, Q.; Liu, B. The synthesis of quinoxalines by condensation reaction of acyloins with o-phenylenediamine without solvent under microwave irradiation. Synth. Commun. 1998, 28, 193-196
26. Rostamizadeh, S.; Jafari, S. Synthesis of quinoxalines under microwave irradiation. Indian J. Heterocycl. Chem. 2001, 10, 303-304
27. Mohsenzadeh, F.; Aghapoor, K.; Darabi, H. R. Benign approaches for the microwave-assisted synthesis of quinoxalines. J. Braz. Chem. Soc. 2007, 18, 297-303.
28. Bhosale, R. S.; Sarda, S. R.; Andhapure, S. S.; Jadhav, W. N.; Bhusare, S. R.; Pawar, R. P. An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst. Tetrahedron Lett. 2005, 46, 7183-7186
29. Dubey, P. K.; Prasada Reddy, P. V. V.; Srinivas, K. One-pot synthesis of 2-(1-alkyl/aralkyl-1 h-benzimidazole-2-yl)-quinoxaline derivatives using molecular iodine. Synth. Commun. 2008, 38, 613-618
30. More, S. V.; Sastry, M. N. V.; Wang, C. C; Yao, C. F. Molecular iodine: A powerful catalyst for the easy and efficient synthesis of quinoxalines. Tetrahedron Lett. 2005, 46, 6345-6348.
31. Robinson, R. S.; Taylor, R. J. K. Quinoxaline synthesis from a-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation. Synlett 2005, 1003-1005
32. Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Org. Biomol. Chem. 2004, 2, 788-796
33. Venkatesh, C; Singh, B.; Mahata, P. K.; Junjappa, H., Iia, H. Heteroannulation of nitroketene N,S-arylaminoacetals with POCl3: A novel highly regioselective synthesis of unsymmetrical 2,3-substituted quinoxalines. Org. Lett. 2005, 7, 2169-2172
34. More, S. V.; Sastry, M. N. V.; Yao, C. F. Cerium(IV) ammonium nitrate (CAN) as a catalyst in tap water: A simple, proficient, and green approach for the synthesis of quinoxalines. Green Chem. 2006, 8, 91-95
35. Darabi, H. R.; Mohandessi, S.; Aghapoor, K.; Mohsenzadeh, F. A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature. Catal. Commun. 2007, 8, 389-392
36. Heravi, M. M.; Taheri, S.; Bakhtiari, K.; Oskooie, H. A. On water: A practical and efficient synthesis of quinoxaline derivatives catalyzed by CuSO4-5H2O. Catal. Commun. 2007, 8, 211-214
37. Huang, T.; Wang, R.; Shi, L.; Lu, X. Montmorillonite K-10: An efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water. Catal. Commun. 2008, 9, 1143-1147
38. Das B., Venkateswarlu K., Suneel K., Majhi A. An efficient and convenient protocol for the synthesis of quinoxalines and dihydropyrazines via cyclization-oxidation processes using HClO4 ■ SiO2 as a heterogeneous recyclable catalyst. Tetrahedron Lett. 2007, 48, 5371-5374
39. Heravi, M. M.; Bakhtiari, K.; Bamoharram, F. F.; Tehrani, M. H. Wells-Dawson type heteropolyacid catalyzed synthesis of quinoxaline derivatives at room temperature. Monatsh Chem. 2007, 138, 465-467
40. Hossein, A.; Oskooie, M. M.; Heravi, K. B.; Shima, T. An efficient and facile synthesis of quinoxaline derivatives catalyzed by KHSO4 at room temperature. Monatsh. Chem. 2007, 138, 875-877
41. Ajeet, K.; Santosh, K.; Amit, S.; Arnab, D.; Subho, M. Ni-nanoparticles: An efficient catalyst for the synthesis of quinoxalines. Catal. Commun. 2008, 9, 778-784
42. Heravi, M. M. Zn[(l)proline]: A powerful catalyst for the very fast synthesis of quinoxaline derivatives at room temperature. Catal. Commun. 2007, 8, 1341-1344
43. Shi, D. Q.; Dou, G. L. Efficient synthesis of quinoxa-line derivatives catalyzed by p-toluenesulfonic acid under solvent-free conditions. Synth. Commun. 2008, 38, 3329-3337.
44. Antoniotti, S.; Dunach, E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines. Tetrahedron Lett. 2002, 43, 3971-3973.
45. Zhou, J. F.; Sun, X. J.; Zhu, F. X.; Li, Y. L.; Gong, G. X. A facile synthesis of 5-arylidene-2-imino-4-thiazolidinones under microwave. Synth. Commun. 2008, 38, 4182-4187; and reference therein.
46. Kappe, G.; Naimi-Janial, M. R. Quantitative cascade condensations between o-phenylenediamines and 1,2-dicarbonyl compounds without production of wastes. Eur. J. Org. Chem. 2002, 1368-1373.
47. Eugene, S.; Barbara, C.; Hazel, B.; Albert, C. Ultraviolet-visible absorption spectra of quinoxaline derivatives. J. Org. Chem. 1957, 22, 625-629.
48. Fleck, E. E. Anhydrous ferric chloride as a rearrangement catalyst for some chlorinated diphenylethanes. J. Org. Chem. 1947, 12, 708-712.
49. Bost, R. W.; Towell, E. E. The preparation of some substituted quinoxalines. J. Am. Chem. Soc. 1948, 70, 903-905.
50. Li, Z. J.; Li, W. S.; Ren, X. H.; Sun, Y. J.; Shi, Y. H.; Ouyang, P. K. Efficient route to quinoxalines catalyzed by sulfamic acid in tap water suspension. Heterocycl. Commun. 2007, 13, 125-130.