One-pot syntheses of dihydro benzo[b][1,4]thiazepines and -diazepines via coupling-isomerization-cyclocondensation sequences

Tetrahedron

Volumn 60, Issue 42, 2004, Pages 9463-9469

  Braun, Roland U ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Catalysis; Cross couplings; Cyclocondensations; Heterocycles; Multicomponent reactions

Indexed keywords

ALCOHOL DERIVATIVE; ANILINE DERIVATIVE; DIAZEPINE DERIVATIVE; HALIDE; THIAZEPINE DERIVATIVE;

ARTICLE; CYCLOCONDENSATION; ELECTRON; ISOMERIZATION; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; X RAY ANALYSIS;

EID: 4544274783     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.001     Document Type: Article

References (41)

1. I. Ugi, A. Dömling, and B. Werner J. Heterocycl. Chem. 37 2000 647 658
2. G.H. Posner Chem. Rev. 86 1986 831 844
3. L. Weber, K. Illgen, and M. Almstetter Synlett 1999 366 374
4. For recent excellent reviews on transition metal assisted sequential transformations and domino processes, see e.g. (a) G. Balme, E. Bossharth, and N. Monteiro Eur. J. Org. Chem. 2003 4101 4111
5. G. Battistuzzi, S. Cacchi, and G. Fabrizi Eur. J. Org. Chem. 2002 2671 2681
6. E.-I. Negishi, C. Copéret, S. Ma, S.-Y. Liou, and F. Liu Chem. Rev. 96 1996 365 393
7. L.F. Tietze Chem. Rev. 96 1996 115 136
8. S. Kobayashi Chem. Soc. Rev. 28 1999 1 15
9. T.J.J. Müller, M. Ansorge, and D. Aktah Angew. Chem., Int. Ed. 39 2000 1253 1256
10. T.J.J. Müller, R. Braun, and M. Ansorge Org. Lett. 2 2000 1967 1970
11. R.U. Braun, K. Zeitler, and T.J.J. Müller Org. Lett. 2 2000 4181 4184
12. R.U. Braun, K. Zeitler, and T.J.J. Müller Org. Lett. 3 2001 3297 3330
13. N.A.M. Yehia, K. Polborn, and T.J.J. Müller Tetrahedron Lett. 43 2002 6907 6910
14. For reviews, see e.g., (a) G.A. Archer, and L.H. Sternbach Chem. Rev. 68 1968 747 784
15. F.D. Popp, and A.C. Noble Adv. Heterocycl. Chem. 8 1967 21 82
16. L.H. Sternbach Angew. Chem. Int. Ed. Engl. 10 1971 34 43
17. J.L. Vanderheyden, and J.E. Vanderheyden J. Pharm. Belg. 36 1981 354 364
18. G.R. Jones, and P.P. Singer Adv. Anal. Toxicol. 2 1989 1 69
19. (f) Bremner, J. B. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 9, pp 183-189.
20. For synthetic and pharmacological studies, see e.g., (a) A. Zellou, Y. Cherrah, M. Hassar, and E.-M. Essassi Ann. Pharm. Fr. 56 1998 169 174
21. F. Savelli, A. Boido, A. Mule, L. Piu, M.C. Alamanni, G. Pirisino, M. Satta, and A. Peana Farmaco 44 1989 125 140
22. A. Nawojski, W. Nawrocka, and H. Liszkiewicz Pol. J. Pharmacol. Pharm. 37 1985 69 72
23. M. Wilimowski, K. Orzechowsa-Juzwenko, J. Barczynska, L. Kedzierska-Gozdzik, M. Witkowska, W. Wojewodzki, E. Dus, T. Plawiak, J. Gryska, and H. Maska Pol. J. Pharmacol. Pharm. 35 1983 89 102
24. V.K. Srivastava, R.K. Satsangi, and K. Kishore Arzneim.-Forsch. 32 1982 1512 1514
25. For synthetic and pharmacological studies, see e.g., (a) K.A. Parker, and A. Dermatakis J. Org. Chem. 62 1997 4164 4167
26. (b) Hargrave, K. D.; Schmidt, G.; Engel, W.; Austel, V. Patent Application: US 91-650141 19910204. Patent Priority: US 89-340937 19890420; US 89-372728 19890628; US 89-438922 19891117; US 90-600554 19901019.
27. R.A. Mane, and D.B. Ingle Indian J. Chem., Sect. B 21B 1982 973 974
28. K.P. Jadhav, and D.B. Ingle Indian J. Chem., Sect. B 22B 1983 180 182
29. A. Attia, O.I. Abdel-Salam, M.H. Abo-Ghalia, and A.E. Amr Egypt. J. Chem. 38 1995 543 554
30. R.J. Reddy, D. Ashok, and P.N. Sarma Indian J. Chem., Sect. B 32B 1993 404 406
31. K. Satyanarayana, and M.N.A. Rao Indian J. Pharm. Sci. 55 1993 230 233
32. G. De Sarro, A. Chimirri, A. De Sarro, R. Gitto, S. Grasso, and M. Zappala Eur. J. Med. Chem. 30 1995 925 929
33. R.H. Swellem, Y.A. Allam, and G.A.M. Nawwar Z. Naturforsch. B 54 1999 1197 1201
34. P.K. Dubey, A. Naidu, C.R. Kumar, and P.V.V.P. Reddy Indian J. Chem. Sect. B 42 2003 1701 1705
35. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-246148 (9b). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223/336-033; e-mail: deposit@ccdc.cam.ac.uk).
36. Organikum, 20th ed.; Becker, H. G. O.; Berger, W.; Domschke, G.; Fanghänel, E.; Faust, J.; Fischer, M.; Gentz, F.; Gewald, K.; Gluch, R.; Mayer, R.; Müller, K.; Pavel, D.; Schmidt, H.; Schollberg, K.; Schwetlick, K.; Seiler, E.; Zeppenfeld, G.; Johann Ambrosius Barth Verlag: Heidelberg, Leipzig, 1996.
37. L. Brandsma Preparative Acetylenic Chemistry 1988 Elsevier Amsterdam
38. N. Krause, and D. Seebach Chem. Ber. 120 1987 1845 1851
39. A. Levai, and R. Bognar Acta Chim. Acad. Sci. Hung. 88 1976 293 297
40. V.D. Orlov, N.N. Kolos, F.G. Yaremenko, and V.F. Lavrushin Chem. Heterocycl. Compd. (Engl. Transl.) 16 1980 547 550
41. V.D. Orlov, N.N. Kolos, and A.F. Abramov Chem. Heterocycl. Compd. (Engl. Transl.) 20 1984 1370 1374