Convenient access to novel functionalized pyrazino[1,2-b]isoquinolin-6-one and diazepino[1,2-b]isoquinolin-7-one scaffolds via the Cushman multicomponent reaction followed by post-condensation

Tetrahedron Letters

Volumn 55, Issue 14, 2014, Pages 2299-2303

  Sarnpitak, Pakornwit ^a   Krasavin, Mikhail ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Aryl glyoxals; Cushman reaction; Deprotection cyclization; Enamines; Post MCR modifications; Scaffold oriented synthesis

Indexed keywords

CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIAZEPINE DERIVATIVE; GLYOXAL DERIVATIVE; ISOQUINOLINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CUSHMAN REACTION; CYCLIZATION; DEPROTECTION REACTION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 84897377470     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.02.099     Document Type: Article

References (39)

1. I. Akritopoulou-Zanze, and S.W. Djuric Heterocycles 73 2007 125 147
2. N. Castagnoli J. Org. Chem. 34 1969 3187 3189
3. M. Cushman, and N. Castagnoli J. Org. Chem. 36 1971 3404 3406
4. M. Cushman, and N. Castagnoli J. Org. Chem. 37 1972 1268 1271
5. M. Cushman, and N. Castagnoli J. Org. Chem. 38 1973 440 448
6. M. Cushman, and N. Castagnoli J. Org. Chem. 39 1974 1546 1550
7. M. Cushman, J. Gentry, and F.W. Dekow J. Org. Chem. 42 1977 286 288
8. M.A. Haimova, N.M. Mollow, S.C. Ivanova, A.I. Dimitrova, and V.I. Ognyanov Tetrahedron 33 1977 331 336
9. There are a few isolated examples of using ketones in the Cushman reaction, see: (a) Adams, C.; Papillon, J.; Ksander, G. M. PCT Int. Appl. WO 2007117982; Chem. Abstr. 2007, 147, 448779.
10. X. Xiao, A. Morrell, P.E. Fanwick, and M. Cushman Tetrahedron 62 2006 9705 9712
11. A. Georgieva, E. Stanoeva, S. Spassov, J. Macicek, O. Angelova, M. Haimova, and N. De Kimpe Tetrahedron 47 1991 3375 3388
12. M.P. Stoyanova, S.E. Angelova, P.Y. Petrov, R.P. Nikolova, and B.L. Shivachev ARKIVOC ii 2010 303 314
13. L. Fodor, J. Szabo, G. Bernath, P. Sohar, D.B. MacLean, R.W. Smith, I. Ninomiya, and T. Naito J. Heterocycl. Chem. 26 1989 333 337
14. Gangloff, A. R.; Litvak, J.; Pararajasingham, K.; Sperandio, D. PCT Int. Appl. WO 2004004727; Chem. Abstr. 2004, 140, 105251.
15. For representative reports on biologically active Cushman reaction derived compounds, see: A.R. Karimi, H.R. Momeni, and R. Pashazadeh Tetrahedron Lett. 53 2012 3440 3443 (neuroprotective)
16. E. Christiansen, C. Urban, M. Grundmann, M.E. Due-Hansen, E. Hagesaether, J. Schmidt, L. Pardo, S. Ullrich, E. Kostenis, M. Kassack, and T. Ulven J. Med. Chem. 54 2011 6691 6703 (antidiabetic)
17. U. Rothweiler, A. Czarna, M. Krajewski, J. Ciombor, C. Kalinski, V. Khazak, G. Ross, N. Skobeleva, L. Weber, and T.A. Holak ChemMedChem 3 2008 1118 1128 (apoptosis inducers)
18. Y. Vara, T. Bello, E. Aldaba, A. Arrieta, J.L. Pizarro, M.I. Arriortua, X. Lopez, and F.P. Cossio Org. Lett. 10 2008 4759 4762 and references cited therein
19. B.M. Trost Angew. Chem., Int. Ed. Engl. 34 1995 259 281
20. M. Cushman, and D.K. Dikshit J. Org. Chem. 45 1980 5064 5067
21. M. Cushman, and Y.P. Gupta Heterocycles 19 1982 1431 1433
22. M. Cushman, A. Abbaspour, and Y.P. Gupta Heterocycles 19 1982 1587 1590
23. M. Cushman, A. Abbaspour, and Y.P. Gupta J. Am. Chem. Soc. 105 1983 2873 2879
24. M. Cushman, and J.-K. Chen J. Org. Chem. 52 1987 1517 1521
25. M. Cushman, P. Mohan, and E.C.R. Smith J. Med. Chem. 27 1984 544 547
26. A. Morrell, M. Placzek, S. Parmley, S. Antony, T.S. Dexheimer, Y. Pommier, and M. Cushman J. Med. Chem. 50 2007 4419 4430
27. M. Conda-Sheridan, P.V.N. Reddy, A. Morrell, B.T. Cobb, C. Marchand, K. Agama, A. Chergui, A. Renaud, A.G. Stephen, L.K. Bindu, Y. Pommier, and M. Cushman J. Med. Chem. 56 2013 182 200
28. M. Conda-Sheridan, E.-J. Park, D.E. Beck, P.V.N. Reddy, T.X. Nguyen, B. Hu, L. Chen, J.J. White, R.B. van Breemen, J.M. Pezzuto, and M. Cushman J. Med. Chem. 56 2013 2581 2605
29. M. Jayaraman, P.E. Fanwick, and M. Cushman J. Org. Chem. 63 1998 5736 5737
30. A. Venkatram, T. Colley, and F. Smith J. Heterocycl. Chem. 42 2005 297 301
31. P.P. Christov, I.D. Kozekov, and M.D. Palamareva J. Heterocycl. Chem. 43 2006 1015 1019
32. M.I. Kandinska, I.D. Kozekov, and M.D. Palamareva Molecules 11 2006 403 414
33. A. Georgieva, E. Stanoeva, S. Spassov, J. Macicek, O. Angelova, M. Naimova, and N. De Kimpe Tetrahedron 47 1991 3375 3388
34. A. Georgieva, E. Stanoeva, K. Karamfilova, S. Spassov, O. Angelova, M. Haimova, N. De Kimpe, and M. Boelens Tetrahedron 50 1994 9399 9410
35. A report on ethyl glyoxylate being used as a Cushman reaction input has appeared in the literature, see: S.F. Hammad, and F.T. Smith J. Heterocycl. Chem. 50 2013 114 119
36. M. Nikulnikov, A. Shumsky, and M. Krasavin Synthesis 2010 2527 2532
37. L.M. Pardo, I. Tellitu, and E. Dominguez Synthesis 2010 971 978
38. Claremon, D. A.; McIntyre, C. J.; Liverton, N. J. PCT Int. Appl. WO2002024655A1; Chem. Abstr. 2002, 136, 263104.
39. F. Song, B. Ren, K. Yu, C. Chen, H. Guo, N. Yang, H. Gao, X. Liu, M. Liu, Y. Tong, H. Dai, H. Bai, J. Wang, and L. Zhang Mar. Drugs 10 2012 1297 1306