Imidazo[l,2-a]quinoxalines accessed via two sequential isocyanide-based multicomponent reactions

Journal of Organic Chemistry

Volumn 74, Issue 6, 2009, Pages 2627-2629

  Krasavin, Mikhail ^a   Shkavrov, Sergey ^a   Parchinsky, Vladislav ^a   Bukhryakov, Konstantin ^a  

^a Chemical Diversity Research Institute   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ISOCYANIDE; MULTI-COMPONENT REACTIONS; QUINOXALINES; SYNTHETIC PROTOCOLS;

CYANIDES;

CARBONYL DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZO[1,2 A]QUINOXALINE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; QUINOXALINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; CYANIDE;

ARTICLE; CHEMICAL REACTION KINETICS; CRYSTALLOGRAPHY; DRUG STRUCTURE; ISOCYANIDE BASED MULTICOMPONENT REACTION; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; CHEMISTRY; SYNTHESIS;

CYANIDES; QUINOXALINES;

EID: 64149097753     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900050k     Document Type: Article

References (27)

1. Dömling, A. Chem. Rev. 2006, 106, 17-89.
2. Ugi, I. Peptides 1980, 2, 365-381.
3. Ilyn, A. P.; Loseva, M. V.; Vvedensky, V. Y.; Putsykina, E. B.; Tkachenko, S. E.; Kiavchenko, D. V.; Khvat, A. V.; Krasavin, M. Y.; Ivachtchenko, A. V. J. Org. Chem, 2006, 71, 2811-2819.
4. Hulme, C.; Lee, Y.-S. Mol. Diversity 2008, 12, 1-15.
5. Kysil, V.; Tkachenko, S.; Khvat, A.; Williams, C.; Tsirulnikov, S.; Churakova, M.; Ivachtchenko. A. Tetrahedron Lett. 2007, 48, 6239-6244.
6. (a) Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 66, 1-663.
7. (b) Blackburn, C.; Guan, B.; Fleming, P.; Shiosaki, K.; Tsai, S. Tetrahedron Lett. 1998, 39, 3635-3638.
8. (a) Shaabani, A.; Maleki, A.; Moghimi-Rad, J. J. Org. Chem. 2007, 72, 6309-6311.
9. (b) Shaabani, A.; Maleki, A.; Mofakham, H.; Khavasi, H. R. J. Comb. Chem. 2008, 10, 323.
10. Recent reviews on post-IMCR chemistries: (a) Akritopoulou-Zanze, I.; Djuric, S. W. Heterocycles 2007, 73, 125-147.
11. (b) Akritopoulou-Zanze, I. Curr. Opin. Chem. Biol. 2008, 12, 324-331.
12. Wessjohann, L. A.; Tran Thi Phuong, T.; WestermannB.,PCT Int. Appl. WO2008022800 (Chem. Abstr. 2008, 148, 285479).
13. For recent examples on relevant methodology by the same group on multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs). see: (a) Rivera, D. G.; Vercillo, O. E.; Wessjohann, L. A. Org. Biomol. Chem. 2008, 6, 1787-1795.
14. (b) Leon, F.; Rivera, D. G.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 1762-1767.
15. Krasavin, M.; Parchinsky, V. Synlett 2008, 645-648.
16. Krasavin, M.; Tsirulnikov. S.; Nikulnikov, M.; Sandulenko, Y.; Bukhryakov. K. Tetrahedron Lett. 2008, 49, 7318-7321.
17. (a) Walborskv, H. M.; Niznik, G. E. J. Am. Chem. Soc. 1969, 91, 7778-7780.
18. (b) Walborskv, H. M.; Niznik, G. E. J. Org. Chem. 1972, 37, 187-191.
19. Sandulenko, Y.; Komarov, A.; Rufanov, K.; Krasavin, M. Tetrahedron Lett. 2008, 49, 5990-5993.
20. Krasavin, M.; Tsirulnikov, S.; Nikulnikov, M.; Kvsil, V.; Ivachtchenko, A. Tetrahedron Lett. 2008, 49, 5241-5243.
21. Parchinsky, V. Z.; Shuvalova, O.; Ushakova, O.; Kravchenko, D. V.; Krasavin, M. Tarahedron Lett. 2006, 47, 947-951.
22. (a) Mandair, G. S.; Light, M.; Russell, A.; Hursthouse, M.; Bradlev, M. Tetrahedron Lett. 2002, 43, 4267-4269.
23. (b) Craballares, S.; Cifuentes, M. M.; Stephenson, G. A. Tarahedron Lett. 2007, 48, 2041-2045.
24. Imidazo[l,2-a]quinoxaline fragment is present in a variety of biologically active compounds with various types of activity, e.g.: (a) Moarbess, G.; DeleuzeMasquefa. C.; Bonnard, V.; Gavraud-Paniagua, S.; Vidal. J.-R.; Bressolle, F.; Pinguet, F.; Bonnet, P.-A. Bioorg. Med. Chem. 2008, 16, 6601-6610.
25. (b) Moarbess, G.; El-Hajj, H.; Kfoury, Y.; El-Sabban, M. E.; Lepelletier, Y.; Hermine, O.; Deleuze-Masquefa, C.; Bonnet, P.-A.; Bazarbachi. A. Blood 2008, 111, 3770-3777.
26. (c) Belema, M.; Bunker, A.; Nguven, V. N.; Beaulieu, F.; Ouellet, C.; Qiu, Y.; Zhang, Y.; Martel, A.; Burke, J. R.; McIntyre, K. W.; Pattoli, M. A.; Daloisio, C.; Gillooly, K. M.; Clarke, W. J.; Brassil, P. J.; Zusi, F. C.; Vyas, D. M. Bioorg. Med. Chem. Lett. 2007, 17, 4284-1289.
27. (d) Deleuze-Masquefa, C.; Gerebtzoff, G.; Subra, G.; Fabreguettes, J.-R.; Ovens, A.; Carraz, M.; Strub, M.-P.; Bompart, J.; George, P.; Bonnet, P.-A. Bioorg. Med. Chem. 2004, 12, 1129-1139.