Stereoselective C(2)-vinylation of 1-substituted imidazoles with 3-phenyl-2-propynenitrile

Journal of Organic Chemistry

Volumn 73, Issue 22, 2008, Pages 9155-9157

  Trofimov, Boris A ^a   Andriyankova, Lyudmila V ^a   Belyaeva, Kseniya V ^a   Mal'kina, Anastasiya G ^a   Nikitina, Lina P ^a   Afonin, Andrei V ^a   Ushakov, Igor A ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ISOMERS;

CARBENE; CHEMICAL EQUATIONS; FUNCTIONALIZED; IMIDAZOL; ROOM TEMPERATURES; STEREOSELECTIVE; VINYL SUBSTITUENTS; VINYLATION; ZWITTERIONIC INTERMEDIATES;

PLANTS (BOTANY);

3 PHENYL 2 PROPYNENITRILE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NITROGEN NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

ACETYLENE; ETHYLENES; IMIDAZOLES; NITRILES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 56449111672     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801240x     Document Type: Article

References (45)

1. (a) Grimmett, M. R. Comprehensive Heterocyclic Chemistry II; Katritsky, A. R., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1966; Vol. 3, pp 77-220.
2. (b) Bellina, F.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 4571-4624.
3. De Luca, L. Curr. Med. Chem. 2006, 13, 1-23.
4. Sennequier, N.; Wolan, D.; Stuehr, D. J. Biol. Chem. 1999, 274, 930-938.
5. (a) Mano, T.; Stevens, R. W.; Ando, K.; Nakao, K.; Okumura, Y.; Sakakibara, M.; Okumura, T.; Tamura, T.; Miyamoto, K. Bioorg. Med. Chem. 2003, 11, 3879-3887.
6. (b) Mano, T.; Okumura, Y.; Sakakibara, M.; Okumura, T.; Tamura, T.; Miyamoto, K.; Stevens, R. W. J. Med. Chem. 2004, 47, 720-725.
7. (a) Hunkeler, W.; Mohler, H.; Pierri, L.; Pole, P.; Bonetti, E. P.; Cumin, R.; Schafinner, R.; Haefely, W. Nature 1981, 290, 514-516.
8. (b) Dyck, B.; Goodfellow, V. S.; Philips, T.; Grey, J.; Haddach, M.; Rowbotton, M.; Naeve, G. S.; Brown, B.; Saunders, J. Bioorg. Med. Chem. Lett. 2004, 10, 1115-1154.
9. Kiselyov, A. S.; Semenova, M.; Semenov, V. V. Bioorg. Med. Chem. Lett. 2006, 16, 1440-1444.
10. Blum, C. A.; Zheng, X.; De Lombaert, S. J. Med. Chem. 2004, 47, 2318-2325.
11. Brogden, R. N.; Heel, R. C.; Speight, T. M.; Avery, G. S. Drugs 1978, 16, 387-417.
12. (a) Niwano, Y.; Seo, A.; Kanai, K.; Hamaguchi, H.; Uchida, K.; Yamaguchi, H. Antimicrob. Agents Chemother. 1994, 38, 2204-2206.
13. (b) Santo, R. Di.; Tafi, A.; Costi, R.; Botta, M.; Artico, M.; Corelli, F.; Forte, M.; Caporuscio, F.; Angiolella, L.; Palamara, A. T. J. Med. Chem. 2005, 48, 5140-5153.
14. Brimblecombe, R. W.; Duncan, W. A. M.; Durant, G. J.; Emmett, J. C.; Gannellin, C. R.; Parsons, M. E. J. Int. Med. Res. 1975, 3, 86-92.
15. Pathan, M. Y.; Paike; V, V.; Pachmase, P. R.; More, S. P.; Ardhapure, S. S.; Pawar, R. P. Arkivoc 2006, Part (xv), 205-210.
16. (a) Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 10th ed; Delgado, J. N., Remers, W. A., Eds.; Lippincott-Raven: Philadelphia, PA, 1998.
17. (b) Coura, J. R. S.; de Castro, L. Mem. Inst. Oswaldo Cruz 2002, 97, 3-24.
18. (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
19. (b) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119.
20. (c) Rahman, T.; Fukuyama, T.; Ryu, I.; Suzuki, K.; Yonemura, K.; Hughes, P. F.; Nokihara, K. Tetrahedron Lett. 2006, 47, 2703-2706.
21. (d) Xu, J.-M.; Liu, B.-K.; Wu, W.-B.; Qian, C.; Wu, Q.; Lin, X.-F. J. Org. Chem. 2006, 71, 3991-3993.
22. (a) Bourissou, D.; Guerret, O.; Gabai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
23. (b) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899-907.
24. (c) Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520-530.
25. (d) Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem. 2007, 46, 2988-3000.
26. (a) Ding, H.; Ma, C.; Yang, Y.; Wang, Y. Org. Lett. 2005, 7, 2125-2127.
27. (b) Trofimov, B. A.; Andriyankova, L. V.; Mal'kina, A. G.; Belyaeva, K. V.; Nikitina, L. P.; Baikalova, L. V. Mendeleev Commun. 2007, 17, 237-238.
28. Rotenberg, A. S.; Panzer, H. P.; Schmitt, J. L.; Card, R. J. Preparation of 2-vinylimidazoles by dehydrogenation of 2-ethylimidazoles and 2-ethylimidazolines. Patent 379608, US, 1983.
29. (a) Lawson, J. K. J. Am. Chem. Soc. 1953, 75, 3398-3400.
30. (b) Kolesnikov, G. S. Synthesis of vinyl derivatives of aromatic and heteroaromatic compounds; Korshak, V. V., Ed.; Akad. Nauk SSSR: Moscow, 1960; pp 244-246 (in Russian).
31. Ohta, S.; Matsukawa, M.; Ohashi, N.; Nagayama, K. Synthesis 1990, 78-81.
32. McNab, H.; Thornley, C. J. Chem. Soc., Perkin Trans. 1 1997, 2203-2209.
33. Popov, I. I.; Narezhnaya, Z. N.; Zubenko, A. A. Khim. Geterotsikl. Soed. 1978, 1104-1107.
34. Ivanova, N. I.; Reutskaya, A. M.; Arbuzova, S. N.; Baikalova, L. V.; Afonin, A. V.; Gusarova, N. K.; Trofimov, B. A. Chem. Heterocycl. Compd. 2002, 221-222.
35. Veronese, A. C.; Vecchiati, G.; Sferra, S.; Orlandini, P. Synthesis 1985, 300-302.
36. (a) Copenhaver, J. W.; Bigelow, M. H. Acetylene and carbon monoxide chemistry; Reinhold Publishing Corp.: New York, 1949.
37. (b) Shostakovsky, M. F.; Skvortsova, G. G.; Glazkova, N. P.; Domnina, E. S. Khim. Geterotsikl. Soed. 1969, 1070-1072.
38. Trofimov, B. A.; Tarasova, O. A.; Shemetova, M. A.; Afonin, A. V.; Klyba, L. V.; Baikalova, L. V.; Mikhaleva, A. I. Zh. Org. Khim. 2003, 39, 437-442.
39. Knölker, H.-J.; Boese, R.; Döring, D.; El-Ahl, A.-A.; Hitzemann, R.; Jones, P. G. Chem. Ber. 1992, 125, 1939-1951.
40. (a) Trofimov, B. A.; Andriyankova, L. V.; Zhivet'ev, S. A.; Mal'kina, A. G.; Voronov, V. K. Tetrahedron Lett. 2002, 43, 1093-1096.
41. (b) Trofimov, B. A.; Andriyankova, L. V.; Shaikhudinova, S. I.; Kazantseva, T. I.; Mal'kina, A. G.; Afonin, A. V. Synthesis 2002, 853-855.
42. Andriyankova, L. V.; Mal'kina, A. G.; Afonin, A. V.; Trofimov, B. A. Mendeleev Commun. 2003, 186-188.
43. Andriyankova, L. V.; Mal'kina, A. G.; Nikitina, L. P.; Belyaeva, K. V.; Ushakov, I. A.; Afonin, A. V.; Nikitin, M. V.; Trofimov, B. A. Tetrahedron 2005, 61, 8031-8034.
44. Trofimov, B. A.; Andriyankova, L. V.; Tlegenov, R. T.; Mal'kina, A. G.; Afonin, A. V.; Il'icheva, L. N.; Nikitina, L. P. Mendeleev Commun. 2005, 33-35.
45. Trofimov, B. A.; Andriyankova, L. V.; Mal'kina, A. G.; Belyaeva, K. V.; Nikitina, L. P.; Dyachenko, O. A.; Kazheva, O. N.; Chekhlov, A. N.; Shilov, G. V.; Afonin, A. V.; Ushakov, I. A.; Baikalova, L. V. Eur. J. Org. Chem. 2007, 1018-1025.