O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles

Journal of Organic Chemistry

Volumn 77, Issue 8, 2012, Pages 3716-3723

  Chaudhari, Pramod S ^a   Pathare, Sagar P ^a   Akamanchi, Krishnacharaya G ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DOMINO REACTIONS; IODOXYBENZOIC ACID; OXADIAZOLES; OXIDATIVE DESULFURIZATION; SYSTEMATIC EXPLORATION; TETRAZOLES; THIADIAZOLES; THIOAMIDES; THIOPHILIC; THIOSEMICARBAZIDES;

DESULFURIZATION; THIOUREAS;

REACTION KINETICS;

1 BENZYL N PROPYL 1H TETRAZOL 5 AMINE; 1 PHENYL 1H TETRAZOL 5 AMINE; 1 PHENYL N PROPYL 1H TETRAZOL 5 AMINE; 5 AMINOTETRAZOLE DERIVATIVE; BENZOIC ACID DERIVATIVE; N 4 BIS(4 METHOXYPHENYL) 4H 1,2,4 TRIAZOL 3 AMINE; N 4 DIPHENYL 4H 1,2,4 TRIAZOLE 3 AMINE; N BENZYL 1 PHENYL 1H TETRAZOL 5 AMINE; N BUTYL 1 PHENYL 1H TETRAZOL 5 AMINE; N CYCLOHEXYL 1 PHENYL 1H TETRAZOL 5 AMINE; N,1 DICYCLOHEXYL 1H TETRAZOL 5 AMINE; N,1 DIPHENYL 1H TETRAZOL 5 AMINE; N,4 BIS(4 CHLOROPHENYL) 4H 1,2,4 TRIAZOL 3 AMINE; O IODOXYBENZOIC ACID; PYRROLE DERIVATIVE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DESULFURIZATION; OXIDATION; SYNTHESIS;

AZOLES; IODOBENZENES; MODELS, CHEMICAL; NITROGEN; OXIDATION-REDUCTION; THIADIAZOLES; TRIAZOLES;

EID: 84860198605     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2025509     Document Type: Article

References (55)

1. Heterocyclic Chemistry; Joule, J. A., Mills, K., Ed.; John Wiley and Sons: Hoboken, NJ, 2010.
2. Zhdankin, V. V. J. Org. Chem. 2011, 76, 1185
3. Satam, V.; Harad, A.; Rajule, R.; Patil, H. Tetrahedron 2010, 66, 7659 and references cited therein
4. Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006, ix, 26
5. Silva, L. F.; Olofsson, B. Nat. Prod. Rep. 2011, 28, 1722
6. Zhu, C.; Xu, D.; Wei, Y. Synthesis 2011, 5, 711
7. Ghosh, H.; Yella, R.; Nath, J.; Patel, B. K. Eur. J. Org. Chem. 2008, 6189
8. Nicolaou, K. C.; Mathison; Casey, J. N.; Montagnon, T. Angew. Chem., Int. Ed. 2003, 42, 4077
9. Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. J. Org. Chem. 2003, 68, 5422
10. Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. Synlett 2005, 9, 1483
11. Patil, P. C.; Bhalerao, D. S.; Dangate, P. S.; Akamanchi, K. G. Tetrahedron Lett. 2009, 50, 5820
12. Chaudhari, P. S.; Dangate, P. S.; Akamanchi, K. G. Synlett 2010, 3065
13. Thomas, J. Ger., Pat. Doc., Offen. 2403357, 1974
14. Chem. Abstr. 1974, 81, 136153.
15. Chapleo, C. B.; Myers, P. L.; Myers, M.; Saville, J. F.; Smith, A. C. B.; Stilling, M. R.; Tulloch, I. F.; Walter, D. S.; Welbourn, A. P. J. Med. Chem. 1986, 29, 2273
16. Yele, H. L.; Losee, K. J. Med. Chem. 1966, 9, 478
17. Ghirian, D.; Schwatz, I.; Smiti, I. Farmacia 1974, 22, 141
18. Zheng, X.; Li, Z.; Wang, Y.; Chen, W.; Huang, Q.; Liu, C.; Song, G. J. Fluorine Chem. 2003, 123, 163
19. Zou, X. J.; Lai, L. H.; Jin, G. Y.; Zhang, Z. X. J. Agric. Food Chem. 2002, 50, 3757
20. Chudgar, N. K.; Shah, S. N.; Vora, R. A. Mol. Cryst. Liq. Cryst. 1989, 172, 51
21. Poindexter, G. S.; Bruce, M. A.; Breitenbucher, J. G.; Higgins, M. A.; Sit, S.-Y.; Romine, J. I.; Mariin, S. W.; Ward, S. A.; McGrovern, R. T.; Clarke, W.; Russel, J.; Antal-Zimanyi, I. Bioorg. Med. Chem. 2004, 12, 507
22. Dumciute, J.; Martynaitis, V.; Holzer, W.; Manelinckx, S.; De Kimpe, N.; Sackus, A, S. Tetrahedron 2006, 62, 3309 and references cited therein
23. Chekler, E. L. P.; Elokdah, A. M.; Butera, J. Tetrahedron Lett. 2008, 49, 6709
24. Dolman, S. J.; Gosselin, F.; Shea, P. D.; Davies, I. W. J. Org. Chem. 2006, 71, 9548 and references cited therein
25. Ishikawa, H.; Elliott, G. I.; Velcicky, J.; Choi, Y.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 10596
26. For biological activities, see: Gupta, J. K.; Dudhey, R.; Sharma, P. K. Medichemonline 2010, 1, 1001
27. Broda, W.; Dehmlow, E. V. Isr. J. Chem. 1985, 26, 219
28. Yamasaki, T.; Furukawa, M. J. Heterocycl. Chem. 1990, 27, 707
29. Hassan, A. A.; Mourad, A. F. E.; El-Shaieb, K. M. Heteroatom Chem. 2003, 14, 535 and references cited therein
30. Hassan, A. A.; Mourad, A. F. E.; El-Shaieb, K. M.; Abou-Zied, A. H. Molecules 2005, 10, 822
31. Yella, R.; Khatun, N.; Rout, S.; Patel, B. K. Org. Biomol. Chem. 2011, 9, 3235
32. Seki, M.; Tarao, Y.; Yamada, K.; Nakao, A.; Usui, Y.; Komatsu, Y. PCT Int. Appl. WO 2005-JP2974, 2005.
33. Chem. Abstr. 2005, 143, 266938.
34. Nonoshita, K.; Ogino, Y.; Ishikawa, M.; Sakai, F.; Nakashima, H.; Nagae, Y.; Tsukahara, D.; Arakawa, K.; Nishimura, T.; Eiki, J. PCT Int. Appl. WO 2004-JP19843, 2005.
35. Chem. Abstr. 2005, 143, 153371.
36. Miao, Z.; Sun, Y.; Nakajima, S.; Tang, D.; Wu, F.; Xu, G.; Or, Y. S.; Wang, Z. US Pat. Appl. Publ. US 2005153877, 2005.
37. Chem. Abstr. 2005, 143, 153709.
38. Luo, G.; Chen, L.; Degnan, A. P.; Dubowchik, G. M.; Macor, J. E.; Tora, G. O.; Chaturvedula, P. V. PCT Int. Appl. WO 2004-US40721, 2005.
39. Chem. Abstr. 2005, 143, 78091.
40. Kozikowski, A. P.; Zhang, J.; Nan, F.; Petukhov, P. A.; Grajkowaska, E.; Wroblewski, J. T.; Yamamoto, T.; Bzdega, T.; Wroblewska, B.; Neale, J. H. J. Med. Chem. 2004, 47, 1729
41. For recent review and procedure, see: Koldobskii, G. I. Russ. J. Org. Chem. 2006, 42, 469
42. Spulak, M.; Lubojacky, R.; Senel, P.; Kunes, J.; Pour, M. J. Org. Chem. 2010, 75, 241 and references cited therein
43. Singh, R. P.; Gao, H.; Meshri, D. T.; Shreeve., J. M. In High Density Materials; Klapotke, T. M., Ed.; Springer: Berlin, 2007; pp 35-83.
44. Tappan, B. C.; Huynh, M. H.; Hiskey, M. A.; Chavez, D. E.; Luther, E. P.; Mang, J. T.; Son, S. F. J. Am. Chem. Soc. 2006, 128, 6589
45. Upadhayaya, R. S.; Jain, S.; Sinha, N.; Kishore, N.; Chandra, R.; Arora, S. K. Eur. J. Med. Chem. 2004, 39, 579
46. For methods of synthesis of 5-aminotetrazoles, see: Katritzky, A. R.; Rogovoy, B. V.; Kovalenko, K. V. J. Org. Chem. 2003, 68, 4941 and references cited therein
47. Lebouvier, N.; Giraud, F.; Corbin, T.; Na, Y. M.; Le Baut, G.; Marchand, P.; Le Borgne, M. Tetrahedron Lett. 2006, 47, 6479
48. Papakonstantinou-Garoufalias, S.; Pouli, N.; Marakos, P.; Chytyroglou-Ladas, A. Farmaco 2002, 57, 973
49. De Clercq, E. J. Clin. Virol. 2004, 30, 115
50. Navidpour, L.; Shadnia, H.; Shafaroodi, H.; Amini, M.; Dehpour, A. R.; Shafiee, A. Bioorg. Med. Chem. 2007, 15, 1976
51. Naito, Y.; Akahoshi, F.; Takeda, S.; Okada, T.; Kajii, M.; Nishimura, H.; Sugiura, M.; Fukaya, C.; Kagitani, Y. J. Med. Chem. 1996, 39, 3019
52. Saha, A. K.; Liu, L.; Simoneaux, R.; DeCorte, B.; Meyer, C.; Skrzat, S.; Breslin, H. J.; Kukla, M. J.; End, D. W. Bioorg. Med. Chem. Lett. 2005, 15, 5154
53. Thompson, S. K.; Eppley, A. M.; Frazee, J. S.; Darcy, M. G.; Lum, R. T.; Tomaszek, T. A.; Ivanoff, L. A.; Morris, J. F.; Sternberg, E. J.; Lambert, D. M.; Fernandez, A. V.; Petteway, S. R.; Meek, T. D.; Metcalf, B. W.; Gleason, J. G. Bioorg. Med. Chem. Lett. 1994, 4, 2441
54. Bibian, M.; Blayo, A. L.; Moulin, A.; Martinez, J.; Fehrentz, J. A. Tetrahedron Lett. 2010, 51, 2660 and references cited therein
55. For recent review and procedures, see: Moulin, A.; Bibian, M.; Blayo, A. L.; Habnouni, S.; Martinez, J.; Fehrentz, J. A. Chem. Rev. 2010, 110, 1809