One-pot synthesis of 7,9-dialkylpurin-8-one analogues: Broad substrate scope

Journal of Organic Chemistry

Volumn 78, Issue 24, 2013, Pages 12629-12636

  Li, Jian Ping ^a   Huang, Yu ^a   Xie, Ming Sheng ^a   Qu, Gui Rong ^a   Niu, Hong Ying ^b   Wang, Hai Xia ^a   Qin, Bo Wen ^a   Guo, Hai Ming ^a  

^a HENAN NORMAL UNIVERSITY   (China)

^b HENAN INSTITUTE OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVES; CATALYTIC SYSTEM; DIRECT SYNTHESIS; HALOGENATED ALKANES; MULTI-STEP; ONE-POT SYNTHESIS; OXIDATION REACTIONS; QUATERNARY AMMONIUM SALT;

CHEMISTRY;

ORGANIC COMPOUNDS;

1 BENZYL 3 ETHYL 1H BENZO[D]IMIDAZOL 2(3H) ONE; 1 BENZYL 3 METHYL 1H BENZO[D]IMIDAZOL 2(3H) ONE; 1,3 DIBENZYL 1H BENZO[D]IMIDAZOL 2(3H) ONE; 6 (1H BENZO[D][1,2,3]TRIAZOL 1 YL) 7,9 DIBENZYL 7H PURIN 8(9H) ONE; 7 ALLYL 9 BENZYL 6 METHOXY 7H PURIN 8(9H) ONE; 7 BENZYL 2 CHLORO 6 PHENOXY 9 PHENYL 7H PURIN 8(9H) ONE; 7 BENZYL 2 CHLORO 9 ISOPROPYL 6 PHENOXY 7H PURIN 8(9H) ONE; 7 BENZYL 9 (2 CHLOROBENZYL) 6 PHENOXY 7H PURIN 8(9H) ONE; 7 BENZYL 9 (SEC BUTYL) 6 PHENOXY 7H PURIN 8(9H) ONE; 7 BENZYL 9 CYCLOPENTYL 6 PHENOXY 7H PURIN 8(9H) ONE; 7 BENZYL 9 ETHYL 6 PHENOXY 7H PURIN 8(9H) ONE; 7 BENZYL 9 METHYL 6 PHENOXY 7H PURIN 8(9H) ONE; 7,9 DIALKYLPURIN 8 ONE DERIVATIVE; 7,9 DIBENZYL 2,6 DIMETHOXY 7H PURIN 8(9H) ONE; 7,9 DIBENZYL 6 (PROPYLTHIO) 7H PURIN 8(9H) ONE; 7,9 DIBENZYL 6 CHLORO 7H PURIN 8(9H) ONE; 7,9 DIBENZYL 6 METHOXY 7H PURIN 8(9H) ONE; 7,9 DIBENZYL 6 PHENOXY 7H PURIN 8(9H) ONE; 9 ALLYL 7 BENZYL 6 PHENOXY 7H PURIN 8(9H) ONE; 9 BENZYL 6 METHOXY 7 METHYL 7H PURIN 8(9H) ONE; 9 BENZYL 6 METHOXY 7 PENTYL 7H PURIN 8(9H) ONE; 9 BENZYL 6 METHOXY 7 PROPYL 7H PURIN 8(9H) ONE; 9 BENZYL 7 (2 BROMOETHYL) 6 METHOXY 7H PURIN 8(9H) ONE; 9 BENZYL 7 (4 BROMOBUTYL) 6 METHOXY 7H PURIN 8(9H) ONE; 9 BENZYL 7 BUTYL 6 METHOXY 7H PURIN 8(9H) ONE; 9 BENZYL 7 ETHYL 6 METHOXY 7H PURIN 8(9H) ONE; ETHYL 2 (9 BENZYL 6 METHOXY 8 OXO 8,9 DIHYDRO 7H PURIN 7YL)ACETIC ACID; ETHYL 2 [7 BENZYL 8 OXO 6 PHENOXY 7H PURIN 9(8H) YL]ACETIC ACID; PURINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; ONE POT SYNTHESIS; OXIDATION; REACTION ANALYSIS; REACTION OPTIMIZATION;

ALKANES; CATALYSIS; COPPER; IODIDES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PURINES; QUATERNARY AMMONIUM COMPOUNDS;

EID: 84890915756     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402248d     Document Type: Article

References (56)

1. Beck, J. P.; Arvanitis, A. G.; Curry, M. A.; Rescinito, J. T.; Fitzgerald, L. W.; Gilligan, P. J.; Zaczek, R.; Trainor, G. L. Bioorg. Med. Chem. Lett. 1999, 9, 967
2. Hirota, K.; Kazaoka, K.; Niimoto, I.; Kumihara, H.; Sajiki, H.; Isobe, Y.; Takaku, H.; Tobe, M.; Ogita, H.; Ogino, T.; Ichii, S.; Kurimoto, A.; Kawakami, H. J. Med. Chem. 2002, 45, 5419
3. Isobe, Y.; Kurimoto, A.; Tobe, M.; Hashimoto, K.; Nakamura, T.; Norimura, K.; Ogita, H.; Takaku, H. J. Med. Chem. 2006, 49, 2088
4. Akee, R. K.; Carroll, T. R.; Yoshida, W. Y.; Scheuer, P. J.; Stout, T. J.; Clardy, J. J. Org. Chem. 1990, 55, 1944
5. Reitz, A. B.; Goodman, M. G.; Pope, B. L.; Argentieri, D. C.; Bell, S. C.; Burr, L. E.; Chourmouzis, E.; Come, J.; Goodman, J. H.; Klaubert, D. H.; Maryanoff, B. E.; Mcdonnell, M. E.; Rampulla, M. S.; Schott, M. R.; Chen, R. J. Med. Chem. 1994, 37, 3561
6. Simic, M. G.; Jovanovic, S. V. J. Am. Chem. Soc. 1989, 111, 5778
7. Guy, A.; Duplaa, A.-M.; Harel, P.; Téoule, R. Helv. Chim. Acta 1988, 71, 1566
8. Bernadou, J.; Gelas, P.; Meunier, B. Tetrahedron Lett. 1988, 29, 6615
9. Kitade, Y.; Nakanishi, R.; Sako, M.; Hirota, K.; Maki, Y. Chem. Pharm. Bull. 1991, 39, 1902
10. Bodepudi, V.; Shibutani, S.; Johnson, F. Chem. Res. Toxicol. 1992, 5, 608
11. Saladino, R.; Crestini, C.; Bernini, R.; Mincione, E.; Ciafrino, R. Tetrahedron Lett. 1995, 36, 2665
12. Madyastha, K. M.; Sridhar, G. R. J. Chem. Soc., Perkin Trans. 1 1999, 677
13. Maruyama, T.; Kozai, S.; Sasaki, F. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 1193
14. Moriguchi, T.; Asai, N.; Wada, T.; Seio, K.; Sasaki, T.; Sekine, M. Tetrahedron Lett. 2000, 41, 5881
15. Sekine, M.; Okada, K.; Seio, K.; Kakeya, H.; Osada, H.; Obata, T.; Sasaki, T. J. Org. Chem. 2004, 69, 314
16. Kutsuma, T.; Sakai, Y.; Ouchi, H.; Shiina, N.; Yamagishi, T.; Shibuya, S.; Yokomatsu, T. Heterocycles 2005, 65, 1967
17. Chatgilialoglu, C.; Navacchiaa, M. L.; Postigo, A. Tetrahedron Lett. 2006, 47, 711
18. Hamm, M. L.; Billig, K. Org. Biomol. Chem. 2006, 4, 4068
19. Aleksandrova, E. V.; Kochergin, P. M. Chem. Heterocycl. Compd. 2009, 45, 1
20. Fleming, A. M.; Kannan, A.; Muller, J. G.; Liao, Y.; Burrows, C. J. J. Org. Chem. 2011, 76, 7953
21. Zaki, M. E. A.; Proenca, M. F. Tetrahedron 2011, 67, 755
22. Sugimura, H.; Nitta, D. Tetrahedron Lett. 2012, 53, 4460
23. Kuethe, J. T.; Wong, A.; Davies, I. W. J. Org. Chem. 2004, 69, 7752
24. McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3311
25. Scott, J. P. Synlett 2006, 2083
26. Zou, B.; Yuan, Q.; Ma, D. Org. Lett. 2007, 9, 4291
27. Li, Z.; Sun, H.; Jiang, H.; Liu, H. Org. Lett. 2008, 10, 3263
28. Zhong, Q.-F.; Sun, L.-P. Tetrahedron 2010, 66, 5107
29. Lach, F.; Koza, P. ACS Comb. Sci. 2012, 14, 491
30. Kameyama, K.; Sako, M.; Hirota, K.; Maki, Y. Synthesis 1983, 849
31. Kitade, Y.; Takeda, Y.; Hirota, K.; Maki, Y. Tetrahedron Lett. 1995, 36, 2633
32. Kitade, Y.; Satio, N.; Kozaki, A.; Takahashi, K.; Yatome, C.; Takeda, Y.; Sajiki, H.; Hirota, K. Nucleosides Nucleotides 1998, 17, 91
33. Xia, R.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2012, 14, 5549
34. Qu, G.-R.; Ren, B.; Niu, H.-Y.; Mao, Z.-J.; Guo, H.-M. J. Org. Chem. 2008, 73, 2450
35. Guo, H.-M.; Rao, W.-H.; Niu, H.-Y.; Jiang, L.-L.; Meng, G.; Jin, J.-J.; Yang, X.-N.; Qu, G.-R. Chem. Commun. 2011, 47, 5608
36. Guo, H.-M.; Jiang, L.-L.; Niu, H.-Y.; Rao, W.-H.; Liang, L.; Mao, R.-Z.; Li, D.-Y.; Qu, G.-R. Org. Lett. 2011, 13, 2008
37. Guo, H.-M.; Yuan, T.-F.; Niu, H.-Y.; Liu, J.-Y.; Mao, R.-Z.; Li, D.-Y.; Qu, G.-R. Chem.-Eur. J. 2011, 17, 4095
38. Qu, G.-R.; Xin, P.-Y.; Niu, H.-Y.; Wang, D.-C.; Ding, R.-F.; Guo, H.-M. Chem. Commun. 2011, 47, 11140
39. Meng, G.; Niu, H.-Y.; Qu, G.-R.; Fossey, J. S.; Li, J.-P.; Guo, H.-M. Chem. Commun. 2012, 48, 9601
40. Qu, G.-R.; Liang, L.; Niu, H.-Y.; Rao, W.-H.; Guo, H.-M.; Fossey, J. S. Org. Lett. 2012, 14, 4494
41. Xin, P.-Y.; Niu, H.-Y.; Qu, G.-R.; Ding, R.-F.; Guo, H.-M. Chem. Commun. 2012, 48, 6717
42. Lee, S.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 13978
43. McLaughlin, E. C.; Doyle, M. P. J. Org. Chem. 2008, 73, 4317
44. Dohi, T.; Takenaga, N.; Goto, A.; Fujioka, H.; Kita, Y. J. Org. Chem. 2008, 73, 7365
45. Würtele, C.; Sander, O.; Lutz, V.; Waitz, T.; Tuczek, F.; Schindler, S. J. Am. Chem. Soc. 2009, 131, 7544
46. Yi, C. S.; Kwon, K.-H.; Lee, D. W. Org. Lett. 2009, 11, 1567
47. Zhou, M.; Schley, N. D.; Crabtree, R. H. J. Am. Chem. Soc. 2010, 132, 12550
48. Sigman, M. S.; Werner, E. W. Acc. Chem. Res. 2012, 45, 874
49. Peng, H.; Lin, A.; Zhang, Y.; Jiang, H.; Zhou, J.; Cheng, Y.; Zhu, C.; Hu, H. ACS Catal. 2012, 2, 163
50. Wei, Y.; Ding, H.; Lin, S.; Liang, F. Org. Lett. 2011, 13, 1674
51. Zhao, Y.; Yim, W.-L.; Tan, C. K.; Yeung, Y.-Y. Org. Lett. 2011, 13, 4308
52. Zhou, M.; Balcells, D.; Parent, A. R.; Crabtree, R. H.; Eisenstein, O. ACS Catal. 2012, 2, 208
53. Zhou, M.; Hintermair, U.; Hashiguchi, B. G.; Parent, A. R.; Hashmi, S. M.; Elimelech, M.; Periana, R. A.; Brudvig, G. W.; Crabtree, R. H. Organometallics 2013, 32, 957
54. Moriyama, K.; Takemura, M.; Togo, H. Org. Lett. 2012, 14, 2414
55. Wu, X.-F. Tetrahedron Lett. 2012, 53, 6123
56. Lima, H. M.; Lovely, C. J. Org. Lett. 2011, 13, 5736