Synthesis of pyrrole-fused chromanones via one-pot multicomponent reactions

Tetrahedron

Volumn 69, Issue 14, 2013, Pages 3054-3060

  Ghandi, Mehdi ^a   Ghomi, Ali Tabatabaei ^a   Kubicki, Maciej ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

3 Acetyl 2H chromen 2 ones; Dihydrochromeno 3,4 c pyrrole 1,4 dione; Isocyanides; Tandem reactions

Indexed keywords

2 CYCLOHEXYL 3 HYDROXY 3 METHYL 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 2 CYCLOHEXYL 3 HYDROXY 3 METHYL 8 NITRO 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 2 CYCLOHEXYL 3 HYDROXY 6 METHOXY 3 METHYL 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 2 TERT BUTYL 3 HYDROXY 3 METHYL 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 2 TERT BUTYL 3 HYDROXY 3 METHYL 8 NITRO 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 2 TERT BUTYL 3 HYDROXY 6 METHOXY 3 METHYL 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 3 HYDROXY 3 METHYL 2 (2,4,4 TRIMETHYLPENTAN 2 YL) 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 3 HYDROXY 3 METHYL 8 NITRO 2 (2,4,4 TRIMETHYLPENTAN 2 YL) 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 3 HYDROXY 6 METHOXY 3 METHYL 2 (2,4,4 TRIMETHYLPENTAN 2 YL) 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 4 CHROMANONE DERIVATIVE; 8 BROMO 2 CYCLOHEXYL 2,3 DIHYDRO 3 HYDROXY 3 METHYLCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 8 BROMO 2 TERT BUTYL 3 HYDROXY 3 METHYL 2,3 DIHYDROCHROMENO[3,4 C]PYRROLE 1,4 DIONE; 8 BROMO 3 HYDROXY 3 METHYL 2 (2,4,4 TRIMETHYLPENTAN 2 YL) 2,3 DIHYDROCHROMENO[4,4 C]PYRROLE 1,4 DIONE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; MICHAEL ADDITION; ONE POT SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 84874659171     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.01.085     Document Type: Article

References (40)

1. B. Liang, S. Kalidindi, J.A. Porco Jr., and C.R.J. Stephenson Org. Lett. 12 2010 572 575
2. B. Ganem Acc. Chem. Res. 42 2009 463 472
3. S.L. Cui, X.F. Lin, and Y.G. Wang Org. Lett. 8 2006 4517 4520
4. K. Kriis, K. Ausmees, T. Pehk, M. Lopp, and T. Kanger Org. Lett. 12 2010 2230 2233
5. A.Y. Shaw, Z. Xu, and C. Hulme Tetrahedron Lett. 53 2012 1998 2000
6. M. Ghandi, N. Zarezadeh, and A. Taheri Tetrahedron Lett. 53 2012 3353 3356
7. M. Ghandi, N. Zarezadeh, and A. Taheri Tetrahedron Lett. 52 2011 1228 1232
8. E. Soleimani, and M. Zainali J. Org. Chem. 76 2011 10306 10311
9. L.E. Kaim, L. Grimaud, and P. Patil Org. Lett. 13 2011 1261 1263
10. A. Shaabani, R. Ghadari, A. Sarvary, and H. Rezayan J. Org. Chem. 74 2009 4372 4374
11. A. Domling Chem. Rev. 106 2006 17 89
12. V. Nair, R.S. Menon, P.B. Beneesh, V. Sreekumar, and S. Bindu Org. Lett. 6 2004 767 769
13. I. Ugi Angew. Chem., Int. Ed. Engl. 1 1962 8 20
14. Z. Song, R.J. Cox, C.M. Lazarus, and T.J. Simpson ChemBioChem 5 2004 1196 1203
15. H. Kakeya, C. Onozawa, M. Sato, K. Arai, and H. Osada J. Med. Chem. 40 1997 391 394
16. S.B. Singh, M.A. Goetz, E.T. Jones, G.F. Bills, R.A. Giacobbe, L. Herram, S. Stevens- Miles, and D.A. Williams Jr. J. Org. Chem. 60 1995 7040 7042
17. Y. Asami, H. Kakeya, R. Onose, A. Yoshida, H. Matsuzaki, and H. Osada Org. Lett. 4 2002 2845 2848
18. C. Che, S. Li, X. Jiang, J. Quan, S. Lin, and Z. Yang Org. Lett. 12 2010 4682 4685
19. J.R. Casley-Smith Br. J. Exp. Pathol. 56 1975 439 443
20. K. Fylaktakidou, D. Hadjipavlou-Litina, K. Litinas, and D. Nicolaides Curr. Pharm. Des. 30 2004 3813 3833
21. T. Neichi, Y. Koshihara, and S.I. Mutora Biochim. Biophys. Acta 753 1983 130 132
22. Y. Kimura, H. Okuda, S. Arichi, K. Baba, and M. Kozawa Biochim. Biophys. Acta 834 1985 224 229
23. P.A. Craven, J. Pfanstiel, and F.R. De Rubertis J. Clin. Invest. 77 1986 850 859
24. Y. Ozaki, T. Ohashi, and Y. Niwa Biochem. Pharmacol. 35 1986 3481 3488
25. M. Paya, B. Halliwell, and J.R.S. Hoult Biochem. Pharmacol. 44 1992 205 214
26. A. Mora, M. Paya, J.L. Rios, and M.J. Alcaraz Biochem. Pharmacol. 40 1990 793 797
27. V. Nair, R.S. Menon, A.U. Vinod, and S. Viji Tetrahedron Lett. 43 2002 2293 2295
28. N. Obata, and T. Takizawa Tetrahedron Lett. 10 1969 3403 3406
29. Y. Ito, H. Kato, and T. Saegusa J. Org. Chem. 47 1982 741 743
30. N.P. Gambarayan, E.M. Rokhlin, Y.V. Zeifmann, L.A. Simonyan, and I.L. Knunyans Dokl. Akad. Nauk SSSR 166 1966 864 868
31. J.H. Rigby, and M.N. Qabar J. Am. Chem. Soc. 113 1991 8975 8976
32. G. Kollenz, W. Ott, E. Ziegler, K. Peters, H.G. v. Schnering, and H. Quast Liebigs Ann. Chem. 1980 1801 1805
33. W. Ott, C. Kratky, and P. Seiler Liebigs Ann. Chem. 1980 1711 1717
34. W. Ott, G. Kollenz, K. Peters, E.-M. Peters, H.G. v. Schnering, and H. Quast Liebigs Ann. Chem. 1983 635 641
35. Crystallographic data for 2b have been deposited at the Cambridge Crystallographic Data Centre with the deposition number CCDC 907693. Copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: 44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk).
36. K.C. Nicolaou, P.S. Baran, Y.-L. Zhong, K.C. Fong, and H.-S. Choi J. Am. Chem. Soc. 124 2002 2190 2201
37. M. Quai, S. Frattini, U. Vendrame, M. Mondoni, S. Dossena, and E. Cereda Tetrahedron Lett. 45 2004 1413 1416
38. M. Adib, M. Mahdavi, M. Alizadeh Noghania, and H.R. Bijanzadeh Tetrahedron Lett. 48 2007 8056 8059
39. M. Ghandi, P. Asgari, A. Taheri, and A. Abbasi Cent. Eur. J. Chem. 8 2010 899 905
40. L.L. Smith, and M.J. Kulig J. Am. Chem. Soc. 98 1976 1027 1029