Iodine-catalyzed stepwise [4+2] cycloaddition of phenothiazine- and ferrocene-containing Schiff bases with DHP promoted by microwave irradiation

Tetrahedron

Volumn 66, Issue 52, 2010, Pages 9938-9944

  Gál, Emese ^a   Cristea, Castelia ^a   Silaghi Dumitrescu, Luminita ^a   Lovász, Tamás ^a   Csámpai, Antal ^b  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

4+2 Cycloaddition; DFT; Frontier molecular orbitals; Iodine catalysis; Microwave assisted reactions

Indexed keywords

10 CHLORO 5 (10 METHYL 10H PHENOTHIAZIN 3 YL) 3,4,4A,5,6,10B HEXAHYDRO 2H PYRANO[3,2 C]QUINOLINE; 2H PYRANO[3,2 C]QUINOLINE DERIVATIVE; 3 (3 HYDROXYPROPYL)QUINOLINE DERIVATIVE; 3 [6 METHOXY 3 [3 (TETRAHYDRO 2H PYRAN2YLOXY) PROPYL]QUINOLIN 2 YL] 10 METHYL 10H PHENOTHIAZINE; 3 [6 METHYL 3 [3 (TETRAHYDRO 2H PYRAN2YLOXY) PROPYL]QUINOLIN 2 YL] 10 METHYL 10H PHENOTHIAZINE; 3,4 DIHYDRO 2H PYRANE; 5 (10 METHYL 10H PHENOTHIAZIN 3 YL) 9 NITRO 3,4,4A,5,6,10B HEXAHYDRO 2H PYRANO[3,2 C]QUINOLINE; 5 FERROCENYL 3 (3 HYDROXYPROPYL) 6 METHOXYQUINOLINE; 6 CHLORO 2 FERROCENYL 3 (3 HYDROXYPROPYL)QUINOLINE; FERROCENE DERIVATIVE; IMINE; IODINE; METHYL 4 (FERROCENYLMETHYLENEAMINO) BENZOATE; METHYL 4 [(10 METHYL 10H PHENOTHIAZIN 3 YL) METHYL ENEAMINO] BENZOATE; METHYL 5 (10 METHYL 10H PHENOTHIAZIN 3 YL) 3,4,4A,5,6,10B HEXAHYDRO 2H PYRANO[3,2 C]QUINOLINE 9 CARBOXYLATE; METHYL 5 FERROCENYL 3 (3 HYDROXYPROPYL)QUINOLINE 6 CARBOXYLATE; PHENOTHIAZINE DERIVATIVE; PYRAN DERIVATIVE; QUINOLINE DERIVATIVE; QUINONE DERIVATIVE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DEHYDROGENATION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; ELECTRON TRANSPORT; MICROWAVE IRRADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ALNUS;

EID: 78649679985     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.046     Document Type: Article

References (59)

1. R.R. Gupta, Phenothiazines and 1,4-Benzothiazines. Chemical and Biomedical Aspects Bioactive Molecules Vol. 4 1988 Elsevier Amsterdam
2. M. Balasubramanian, and J.G. Keay A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Pergamon Oxford 245
3. G.J. Atwell, B.C. Baguley, and W.A. Denny J. Med. Chem. 32 1989 396
4. R.W. Carling, P.D. Leeson, A.M. Moseley, R. Baker, A.C. Forster, S. Grimwood, J.A. Kemp, and G.R. Marshall J. Med. Chem. 35 1992 1942
5. B. Weber, A. Serafin, J. Michie, C. Van Rensburg, C.J. Swarts, and L. Bohm Anticancer Res. 24 2004 763 (2B)
6. G. Jaouen, S. Top, A. Vessieres, G. Leclercq, and M.J. McGlinchey Curr. Med. Chem. 11 2004 2505
7. V. Zsoldos-Mády, A. Csámpai, R. Szabó, E. Mészáros-Alapi, J. Pásztor, F. Hudecz, and P. Sohár ChemMedChem 1 2006 1119
8. T. Klimova, E.I. Klimova, M. Martinez Garcia, E.A. Vázquez López, C. Alvarez Toledano, A.R. Toscano, and L. Ruíz Ramírez J. Organomet. Chem. 628 2001 107
9. E. Hillard, A. Vessieres, L. Thouin, G. Jaouen, and C. Amatore Angew. Chem., Int. Ed. 45 2006 285
10. I. Damljanović, M. Vukićević, N. Radulović, R. Palić, E. Ellmerer, Z. Ratković, M.D. Joksović, and R.D. Vukićević Bioorg. Med. Chem. Lett. 19 2009 1093
11. M.D. Joksović, V. Marković, Z.D. Juranić, T. Stanojković, L.S. Jovanović, I.S. Damljanović, K. Mészáros Szécsényi, N. Todorović, S. Trifunović, and R.D. Vukićević J. Organomet. Chem. 694 2009 3935
12. C. Biot, G. Glorian, L.A. Maciejewski, and J.S. Brocard J. Med. Chem. 40 1997 3715
13. Representative references reporting on the activity of phenothiazine radicals:
14. P. Holt Sackett, and R.L. McCreery J. Med. Chem. 22 1979 1447
15. K. Kawai, T. Takada, S. Tojo, and T. Majima Tetrahedron Lett. 43 2001 89
16. S. Muraoka, and T. Miura Pharmacol. Toxicol. 92 2003 100
17. J. Gutierrez-Correa, R.L. Krauth-Siegel, and A.O.M. Stoppani Free Radical Res. 37 2003 281
18. D.R. Striplin, S.Y. Reece, D.G. McCafferty, C.G. Wall, D.A. Friesen, B.W. Erickson, and T.J. Meyer J. Am. Chem. Soc. 126 2004 5282
19. Representative references reporting on the activity of ferricenium radicals:
20. P. Koepf-Maier, H. Koepf, and E.W. Neuse J. Cancer Res. Clin. Oncol. 108 1984 336
21. E.W. Neuse, and F. Kanzawa Appl. Organomet. Chem. 4 1990 19
22. H. Tamura, and M. Miwa Org. Lett. 11 1997 1177
23. G. Caldwell, M.G. Meirim, E.W. Neuse, and C.E.J. Van Rensburg Appl. Organomet. Chem. 12 1998 793
24. B. Kuchler, A.G. Abdel-Ghany, P. Bross, A. Nandy, I. Rasched, and S. Ghisla Biochem. J. 337 1999 225
25. E.W. Neuse Macromol. Symp. 172 2001 127
26. X.-F. Lin, S.-L. Cui, and Y.-G. Wang Tetrahedron Lett. 47 2006 3127
27. M. Zora, and Ö Velioglu J. Organomet. Chem. 693 2008 2159
28. J.S. Yadav, B.V.S. Reddy, C.R. Madhuri, and G. Sabitha Synthesis 7 2001 1065
29. G. Babu, and P.T. Perumal Tetrahedron Lett. 39 1998 3225
30. B. Crousse, J.P. Begue, and D.B. Delpon Tetrahedron Lett. 39 1998 5765
31. Y. Ma, C. Qian, M. Xie, and J. Sun J. Org. Chem. 64 1999 6462
32. C.T. Magesh, S.V. Makesh, and P.T. Perumal Bioorg. Med. Chem. Lett. 2004 2035
33. M. Hadden, and P.J. Stevenson Tetrahedron Lett. 40 1999 1215
34. S. Kobayashi, M. Sugiura, H. Kitagawa, and W. Lam Chem. Rev. 102 2002 2227
35. G. Sundararajan, N. Prabagaran, and B. Varghese Org. Lett. 3 2001 1973
36. T.L. Gilchrist, and A.M. Stannard Tetrahedron Lett. 29 1988 3538
37. M. Makesh, C.V. Reddy, K. Reddy, R.P. Srinavasa, and V.V.N. Reddy Synth. Commun. 34 2004 4089
38. L.C. da Silva-Filho, V. Lacerda Jr., M.G. Constantino, and G.V. Jose da Silva Synthesis 16 2008 2527
39. A.V.R. Narsaiah, A.R. Reddy, BV.S. Reddy, and J.S. Yadav Synth. Commun. 40 2010 1750
40. K. Nagaiah, D. Sreemu, R. Rao, V.G. Srininasa, and J.S. Yadav Tetrahedron Lett. 47 2006 4409
41. B. Das, P. Balasubramanyam, M. Krishnaiah, and B. Veeranjaneyulu Synth. Commun. 39 2009 3825
42. V. Sindharan, C. Avendano, and J.C. Menendez Synthesis 7 2008 1039
43. J. Li, J. Li, and W. Su J. Chem. Res. 8 2009 499
44. Y.-C. Li, J.-M. Zhang, and L.-T. Dong Chin. J. Chem. 24 2006 929
45. G. Jin, J. Zhao, J. Han, S. Zhu, and J. Zhang Tetrahedron 66 2010 913
46. M. Xia, and Y.-D. Lu Synlett 15 2005 2357
47. X. Xing, J. Wu, and W.M. Dai Tetrahedron 62 2006 11200
48. E. Gál, L. Gin, T. Lovász, C. Cristea, and L. Silaghi-Dumitrescu Stud. Univ. Babes-Bolyai, Chem. 4 2009 17
49. C.V.O. Imrie, T.I. Nyamori, and A. Gerber J. Organomet. Chem. 689 2004 1617
50. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford, University New York, NY
51. T. Zeigler Chem. Rev. 91 1991 651
52. A.D. Becke J. Chem. Phys. 98 1993 5648
53. C. Lee, W. Yang, and R.G. Parr Phys Rev. B 37 1988 785
54. N. Godbout, D.R. Salahub, J. Andzelm, and E. Wimmer Can. J. Chem. 70 1992 560
55. G. Klopman J. Am. Chem. Soc. 90 1968 223
56. L.E. Overman, and J.P. Wolfe J. Org. Chem. 66 2001 3161
57. H. Braunschweig, K. Radacki, D. Rais, and F. Seeler Organometallics 23 2004 5545
58. M. Scheibitz, M. Bolte, J.W. Bats, H.-W. Lerner, I. Nowik, R.H. Herber, A. Krapp, M. Lein, M.C. Holthausen, and M. Wagner Chem. - Eur. J. 11 2004 584
59. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven Jr., K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzales, and J.A. Pople GAUSSIAN 03, Revision A. 1 2003 Gaussian Pittsburgh, PA