Keywords
11-oxo-6,11,12,13-tetrahydrodibenzo[b,g][1,5]oxazonine
compound library
parallel synthesis
Ugi MCR
Abstract
A convenient synthesis of rare diaryl-fused nine-membered heterocyclic scaffold using a novel modification of four-component Ugi condensation based on the usage of aromatic aldehyde-acid as bifunctional component is described.
References
1.
N-formyl hydroxylamine containing dipeptides: generation of a new class of vasopeptidase inhibitors.
Robl J.A., Simpkins L.M., Asaad M.M.
Bioorganic and Medicinal Chemistry Letters,
2000
2.
D. J. Lauffer, M. D. Mullican, M. W. Wannamaker, A. L. C. Robidoux, D. J. Livingston, J. M. C. Golec and P. L. Nyce, US Patent, 6350741. (Chem. Abstr., 2002, 129, 054607d).
3.
J. Rosamond, C. Becker, J.Woods, B. Dembofsky, J. Kang, C. Ohnmacht, T. Simpson, A. B. Shenvi and R. Jacobs, WO Patent, 0431154, 2004.
4.
P. Bühlmayer and P. Furet, US Patent, 5610153. (Chem. Abstr., 1995, 122, 214113a).
5.
A. A. Nagel, WO Patent, 9401421. (Chem. Abstr., 1996, 125, 115153u).
6.
Murakami Y., Hara H., Okada T., Hashizume H., Kii M., Ishihara Y., Ishikawa M., Shimamura M., Mihara S., Kato G., Hanasaki K., Hagishita S., Fujimoto M.
Journal of Medicinal Chemistry,
1999
7.
H. Fukui, S. Ikegami, M. Watanuki, T. Maruyama, Y. Sumita and K. Inoguchi, WO Patent, 0155121, 2001.
8.
H. Yukimasa, R. Tozawa, M. Kori and K. Kitano, US Patent, 5726306. (Chem. Abstr., 1994, 120, 164246g).
9.
J. Gante, H. Juraszyk, P. Raddatz, H. Wurziger, G. Melzer and B. S. Danielowski, US Patent, 6028090. (Chem. Abstr., 1995, 123, 198781e).
10.
M. Hellberg, G. Graff, D. A. Gamache, J. C. Nixon and W. H. Garner, EP Patent, 0799219. (Chem. Abstr., 1996, 125, 167788z).
11.
E. S. Hamanaka, J. M. Hawkins and C. M. Hayward, US Patent, 5770594. (Chem. Abstr., 1996, 125, 168038s).
12.
R. C. Gadwood and B. V. Kamdar, EP Patent, 1019385. (Der. Abstr., 1997, C1997, 212522).
13.
E. C. Taylor, C. Shih, K. Lee and L. S. Gossett, WO Patent, 9741115. (Chem. Abstr., 1998, 128, 003888t).
14.
J. D. Rodgers and A. J. Cocuzza, US Patent, 6140320. (Chem. Abstr., 1998, 130, 237598s).
15.
Sica D.A.
Journal of Clinical Hypertension,
2005
16.
Cale A.D., Gero T.W., Walker K.R., Lo Y.S., Welstead W.J., Jaques L.W., Johnson A.F., Leonard C.A., Nolan J.C., Johnson D.N.
Journal of Medicinal Chemistry,
1989
17.
A. D. Cale, Jr., US Patent, 4592866. (Chem. Abstr., 1984, 101, 130726f).
18.
T. Kaya, W.Watanabe and T. Inaba, WO Patent, 03024941. (Der. Abstr., 2003, C2003, 313340).
19.
Hansen J., Klimek L., H??rmann K.
Drugs and Aging,
2005
20.
Gaudy-Marqueste C., Grob J.-., Richard M.-.
Annales de Dermatologie et de Venereologie,
2005
21.
Klunder J.M., Hargrave K.D., West M., Cullen E., Pal K., Behnke M.L., Kapadia S.R., McNeil D.W., Wu J.C., Chow G.C., Adams J.
Journal of Medicinal Chemistry,
1992
22.
Aiello F., Brizzi A., Garofalo A., Grande F., Ragno G., Dayam R., Neamati N.
Bioorganic and Medicinal Chemistry,
2004
23.
I. Ugi, Isonitrile Chemistry, Academic Press, London, 1971.
24.
Ugi I., Dömling A., Hörl W.
Endeavour,
1994
25.
R.W. Armstrong, D. S. Brown, T. A. Keating and P. A. Tempest, in Combinatorial Chemistry Synthesis and Application, eds. S.Wilson and A.W. Czarnik, John Wiley and Sons, New York, 1997, p. 153.
26.
Armstrong R.W., Combs A.P., Tempest P.A., Brown S.D., Keating T.A.
Accounts of Chemical Research,
1996
27.
Zhang J., Jacobson A., Rusche J.R., Herlihy W.
Journal of Organic Chemistry,
1999
28.
Lee D., Sello J.K., Schreiber S.L.
Organic Letters,
2000
29.
Ley S.V., Taylor S.J.
Bioorganic and Medicinal Chemistry Letters,
2002
30.
Marcaccini S., Pepino R., Torroba T., Miguel D., Garcı́a-Valverde M.
Tetrahedron Letters,
2002
31.
Marcaccini S., Miguel D., Torroba T., García-Valverde M.
Journal of Organic Chemistry,
2003
32.
Ilyin A.P., Trifilenkov A.S., Kurashvili I.D., Krasavin M., Ivachtchenko A.V.
Journal of Combinatorial Chemistry,
2005
33.
Ilyn A.P., Kuzovkova J.A., Potapov V.V., Shkirando A.M., Kovrigin D.I., Tkachenko S.E., Ivachtchenko A.V.
Tetrahedron Letters,
2005
34.
Ilyn A.P., Trifilenkov A.S., Tsirulnikov S.A., Kurashvily I.D., Ivachtchenko A.V.
Journal of Combinatorial Chemistry,
2005
35.
Ilyin A.P., Kobak V.V., Dmitrieva I.G., Peregudova Y.N., Kustova V.A., Mishunina Y.S., Tkachenko S.E., Ivachtchenko A.V.
European Journal of Organic Chemistry,
2005
36.
Ilyin A.P., Kobak V.V., Dmitrieva I.G., Peregudova Y.N., Kustova V.A., Mishunina Y.S., Tkachenko S.E., Ivachtchenko A.V.
Synthetic Communications,
2006
37.
Ilyn A.P., Trifilenkov A.S., Kovrigin D.I., Yudin M.V., Ivachtchenko A.V.
Heterocyclic Communications,
2006
38.
Ilyn A.P., Kuzovkova J.A., Shkirando A.M., Ivachtchenko A.V.
Heterocyclic Communications,
2005
39.
Ilyin A.P., Parchinski V.Z., Peregudova J.N., Trifilenkov A.S., Poutsykina E.B., Tkachenko S.E., Kravchenko D.V., Ivachtchenko A.V.
Tetrahedron Letters,
2006
40.
Ilyn A.P., Loseva M.V., Vvedensky V.Y., Putsykina E.B., Tkachenko S.E., Kravchenko D.V., Khvat A.V., Krasavin M.Y., Ivachtchenko A.V.
Journal of Organic Chemistry,
2006
41.
S. E. Tkachenko, A. P. Ilyin and A. V. Ivachtchenko, in Proc. 20th International Congress of Heterocyclic Chemistry, Palermo, 2005, 2-PO4, p. 317.
42.
A. P. Ilyin, J. A. Kuzovkova and A. V. Ivachtchenko, in Proc. 20th International Congress of Heterocyclic Chemistry, Palermo, 2005, 2-PO9, p. 322.
43.
J. A. Kuzovkova and A. V. Ivachtchenko, in Proc. 20th International Congress of Heterocyclic Chemistry. Palermo, 2005, 2-PO11, p. 324.
44.
V. Kysil, A. V. Khvat, C. Williams, S. E. Tkachenko, A. P. Ilyin and A. V. Ivachtchenko, in Proc. 3rd International Conference on Multi-Component Reactions and Related Chemistry, Amsterdam, 2006, p. 102.
45.
S. Tkachenko, A. Ivachtchenko, A. Khvat, C. Williams, A. Ilyin and V. Kysil, in Book of the 21st International Congress for Heterocyclic Chemistry. Program and Abstract Book. The University of New South Wales, 2007, TP118, p. 296.
46.
Ilyn A.P., Trifilenkov A.S., Kuzovkova J.A., Kutepov S.A., Nikitin A.V., Ivachtchenko A.V.
Journal of Organic Chemistry,
2005
47.
Potapov V.V., Fetisova N.A., Nikitin A.V., Ivachtchenko A.V.
Tetrahedron Letters,
2009
48.
Guillaumel J., Boccara N., Demerseman P.
Journal of Heterocyclic Chemistry,
1990
49.
Harriman G.C.
Tetrahedron Letters,
1997
50.
Short K.M., Mjalli A.M.
Tetrahedron Letters,
1997