Click chemistry with 2-ethynyl-4,5,6,7-tetrahydroindoles: Towards functionalized tetrahydroindole-triazole ensembles

Synthesis (Germany)

Volumn 45, Issue 5, 2013, Pages 678-682

  Sobenina, Lyubov N ^a   Tomilin, Denis N ^a   Ushakov, Igor A ^a   Mikhaleva, Albina I ^a   Ma, J Sh ^b   Yang, G ^b   Trofimov, Boris A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

alkynes; click chemistry; cycloaddition; sodium azide; triazoles

Indexed keywords

ALKYNES; CLICK CHEMISTRY; ESTER MOIETIES; FUNCTIONALIZED; QUANTITATIVE YIELDS; ROOM TEMPERATURE; SODIUM AZIDE; TRIAZOLES;

ACETYLENE; CYCLOADDITION; SODIUM;

SYNTHESIS (CHEMICAL);

2 ETHYNYL 4,5,6,7 TETRAHYDROINDOLE DERIVATIVE; ACETYLENE DERIVATIVE; BROMOACETYLENE DERIVATIVE; CARBON; DIMETHYL SULFOXIDE; ESTER DERIVATIVE; ETHYL 5 (1 BENZYL 4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 CARBOXYLATE; ETHYL 5 (1 METHYL 4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 CARBOXYLATE; ETHYL 5 (1 VINYL 4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 CARBOXYLATE; ETHYL 5 (4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 CARBOXYLATE; INDOLE DERIVATIVE; PHENYL [5 (1 BENZYL 4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 YL]METHANONE; PHENYL [5 (1 METHYL 4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 YL]METHANONE; PHENYL [5 (1 VINYL 4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 YL]METHANONE; PHENYL [5 (4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 3H 1,2,3 TRIAZOL 4 YL]METHANONE; POTASSIUM CARBONATE; SODIUM AZIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CLICK CHEMISTRY; CYCLOADDITION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; INFRARED SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; QUANTITATIVE ANALYSIS; ROOM TEMPERATURE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 84874269145     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1318149     Document Type: Article

References (66)

1. Kharb, R.; Sharma, P. Ch.; Yar, M. Sh. J. Enzyme Inhib. Med. Chem. 2011, 26, 1.
2. Singhal, N.; Sharma, P. K.; Dudhe, R.; Kumar, N. J. Chem. Pharm. Res. 2011, 3, 126.
3. Bektaş, H.; Karaali, N.; Sahin, D.; Demirbaş, A.; Karaoglu, S. A.; Demirbaş, N. Molecules 2010, 15, 2427.
4. Sumangala, V.; Poojary, B.; Chidananda, N.; Fernandes, J.; Kumari, N. S. Arch. Pharmacal. Res. 2010, 33, 1911.
5. Pereira, D.; Fernandes, P. Bioorg. Med. Chem. Lett. 2011, 21, 510.
6. Savini, L.; Massarelli, P.; Chiasserini, L.; Pellerano, C.; Bruni, G. Farmaco 1994, 49, 633.
7. Almasirad, A.; Tabatabai, S. A.; Faizi, M.; Kebriaeezadeh, A.; Mehrabi, N.; Dalvandi, A.; Shafiee, A. Bioorg. Med. Chem. Lett. 2004, 14, 6057.
8. Ram, J. S. Rasayan J. Chem. 2009, 2, 706.
9. Rajasekaran, A.; Rajagopal, K. A. Acta Pharm. 2009, 59, 355.
10. Singh, B. K.; Yadav, A. K.; Kumar, B.; Gaikwad, A.; Sinha, S. K.; Chaturvedi, V.; Tripathi, R. P. Carbohydr. Res. 2008, 343, 1153.
11. Wilkinson, B. L.; Long, H.; Sim, E.; Fairbanks, A. J. Bioorg. Med. Chem. Lett. 2008, 18, 6265.
12. Boechat, N.; Ferreira, V. F.; Ferreira, S. B.; de Lourdes, G.; Ferreira, M.; de C da Silva, F.; Bastos, M. M.; Dos, S.; Costa, M.; Lourenço, M. C.; Pinto, A. C.; Krettli, A. U.; Aguiar, A. C.; Teixeira, B. M.; da Silva, N. V.; Martins, P. R.; Bezerra, F. A.; Camilo, A. L.; da Silva, G. P.; Costa, C. C. J. Med. Chem. 2011, 54, 5988.
13. Zhou, L.; Amer, A.; Korn, M.; Burda, R.; Balzarini, J.; De Clercq, E.; Kern, E. R.; Torrence, P. F. Antiviral Chem. Chemother. 2005, 16, 375.
14. Jordão, A. K.; Afonso, P. P.; Ferreira, V. F.; de Souza, M. C.; Almeida, M. C.; Beltrame, C. O.; Paiva, D. P.; Wardell, S. M.; Wardell, J. L.; Tiekink, E. R.; Damaso, C. R.; Cunha, A. C. Eur. J. Med. Chem. 2009, 44, 3777.
15. Pérez-Castro, I.; Caamaño, O.; Fernández, F.; García, M. D.; López, C.; de Clercq, E. ARKIVOC 2010, (iii), 152.
16. Holla, B. S.; Poojary, K. N.; Rao, B. S.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511.
17. Holla, B. S.; Veerendra, B.; Shivananda, M. K.; Poojary, B. Eur. J. Med. Chem. 2003, 38, 759.
18. Reddy, D. M.; Srinivas, J.; Chashoo, G.; Saxena, A. K.; Kumar, H. M. S. Eur. J. Med. Chem. 2011, 46, 1983.
19. Singh, P.; Raj, R.; Kumar, V.; Mahajan, M. P.; Bedi, P. M.; Kaur, T.; Saxena, A. K. Eur. J. Med. Chem. 2012, 47, 594.
20. Li, X.; Lin, Y.; Yuan, Y.; Liu, K.; Qian, X. Tetrahedron 2011, 67, 2299.
21. Kumar, D.; Narayanam, M. K.; Chang, K.-H.; Shah, K. Chem. Biol. Drug Des. 2011, 77, 182.
22. Kaur, H.; Kumar, S.; Lata, S.; Saxena, K. K.; Kumar, A. Eur. J. Med. Chem. DOI: 10.1016/j.ejmech.2010.07.047.
23. Aher, N. G.; Pore, V. S.; Mishra, N. N.; Kumar, A.; Shukla, P. K.; Sharma, A.; Bhat, M. K. Bioorg. Med. Chem. Lett. 2009, 19, 759.
24. Wei, J.-J.; Jin, L.; Wan, K.; Zhou, Ch.-He. Bull. Korean Chem. Soc. 2011, 32, 229.
25. Sangshetti, J. N.; Lokwani, D. K.; Sarkate, A. P.; Shinde, D. B. Chem. Biol. Drug Des. 2011, 78, 800.
26. Morzherin, Y.; Prokhorova, P. E.; Musikhin, D. A.; Glukhareva, T. V.; Fan, Z. Pure Appl. Chem. 2011, 83, 715.
27. Shalini, K.; Kumar, N.; Drabu, S.; Sharma, P. K. Beilstein J. Org. Chem. 2011, 7, 668.
28. Wang, X. L.; Wan, K.; Zhou, C. H. Eur. J. Med. Chem. 2010, 45, 4631.
29. Schreier, E. Helv. Chim. Acta 1976, 59, 585.
30. Dong, H.-S.; Wei, K.; Wang, Q.-L.; Quan, B.; Zhang, Z.-Y. J. Chin. Chem. Soc. 2000, 47, 343.
31. The Merck Index, 12th ed.; Budavari, S., Ed.; Merck Co. Inc: White House Station, NJ, 1996.
32. Haber, J. Cas. Lek. Cesk. 2001, 140, 596.
33. Mothes-Wagner, U.; Reitze, H. K.; Seitz, K. A. Exp. Appl. Acarol. 1990, 8, 27.
34. Pechacek, J. T. US Patent 6015826 A, 1998; Chem. Abstr. 2000, 132, 89499.
35. Jacobson, R. M.; Mulvihill, M. J.; Liu, Ch.; Liu, X. US Patent 6258751, 2001; Chem. Abstr. 2001, 134, 42133.
36. Quraishi, M. A.; Danish, J. J. Am. Oil Chem. Soc. 2000, 77, 1107.
37. Quraishi, M. A.; Sardar, R. Corrosion 2002, 58, 748.
38. Khanmohammadi, H.; Erfantalab, M. Spectrochim. Acta, Part A 2012, 86, 39.
39. Smith, N. W.; Alonso, A.; Brown, C. M.; Dzyuba, S. V. Biochem. Biophys. Res. Commun. 2010, 391, 1455.
40. Guenther, D.; Nestler, H. J.; Roesher, G.; Schinzel, E. Ger. Pat. 615164, 1980; Chem. Abstr. 1980, 93, 73786.
41. Bijev, A. T.; Prodanova, P. Chem. Heterocycl. Compd. 2007, 43, 306.
42. Padmavathi, V.; Nagendra, Mohan. A. V.; Thriveni, P.; Shazia, A. Eur. J. Med. Chem. 2009, 44, 2313.
43. Sessler, J. L.; Cai, J.; Gong, H.-Y.; Yang, X.; Arambula, J. F.; Hay, B. P. J. Am. Chem. Soc. 2010, 132, 14058.
44. Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786.
45. Amantini, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F.; Zunino, E.; Vaccaro, L. J. Org. Chem. 2005, 70, 6526.
46. Barluenga, J.; Valdés, C.; Beltrán, G.; Escribano, M.; Aznar, F. Angew. Chem. Int. Ed. 2006, 45, 6893.
47. Jiang, Y.; Kuang, C.; Yang, Q. Synthesis 2010, 4256.
48. Kolarovič, A.; Schnürch, M.; Mihovilovic, M. D. J. Org. Chem. 2011, 76, 2613.
49. Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117.
50. Katritzky, A. R.; Singh, S. K. J. Org. Chem. 2002, 67, 9077.
51. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
52. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Heterocycles 2003, 60, 1225.
53. Li, J.; Wang, D.; Zhang, Y.; Li, J.; Chen, B. Org. Lett. 2009, 11, 3024.
54. Wu, L.-Y.; Xie, Y.-X.; Chen, Z.-S.; Niu, Y.-N.; Liang, Y.-M. Synlett 2009, 1453.
55. Zhang, W.; Kuang, C.; Yang, Q. Synthesis 2010, 283.
56. Trofimov, B. A.; Stepanova, Z. V.; Sobenina, L. N.; Mikhaleva, A. I.; Ushakov, I. A. Tetrahedron Lett. 2004, 45, 6513.
57. Stepanova, Z. V.; Sobenina, L. N.; Mikhaleva, A. I.; Ushakov, I. A.; Elokhina, V. N.; Voronov, V. K.; Trofimov, B. A. Synthesis 2004, 2736.
58. Sobenina, L. N.; Demenev, A. P.; Mikhaleva, A. I.; Ushakov, I. A.; Vasil'tsov, A. M.; Ivanov, A. V.; Trofimov, B. A. Tetrahedron Lett. 2006, 47, 7139.
59. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Demenev, A. P.; Mikhaleva, A. I.; Ushakov, I. A.; Vakul'skaya, T. I.; Petrova, O. V. Russ. J. Org. Chem. 2006, 42, 1348.
60. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Ushakov, I. A.; Petrova, O. V.; Tarasova, O. A.; Volkova, K. A.; Mikhaleva, A. I. Synthesis 2007, 447.
61. Trofimov, B. A.; Sobenina, L. N.; Demenev, A. P.; Stepanova, Z. V.; Petrova, O. V.; Ushakov, I. A.; Mikhaleva, A. I. Tetrahedron Lett. 2007, 48, 4661.
62. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Vakul'skaya, T. I.; Kazheva, O. N.; Aleksandrov, G. G.; Dyachenko, O. A.; Mikhaleva, A. I. Tetrahedron 2008, 64, 5541.
63. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Petrova, O. V.; Ushakov, I. A.; Mikhaleva, A. I. Tetrahedron Lett. 2008, 49, 3946.
64. Trofimov, B. A.; Mikhaleva, A. I. N-Vinylpyrroles; Nauka: Novosibirsk, 1984.
65. Trofimov, B. A. In Advances in Heterocyclic Chemistry; Vol. 51; Academic Press: New York, 1990, 177.
66. Trofimov, B. A.; Mikhaleva, A. I.; Schmidt, E. Yu.; Ryapolov, O. A.; Platonov, V. B. Russian Patent RU 2297410, 2006; Chem. Abstr. 2008, 146, 462130.