Isomerization and ring-closing metathesis for the synthesis of 6-, 7- and 8-membered benzo- and pyrido-fused N,N-, N,O- and N,S-heterocycles

Tetrahedron Letters

Volumn 45, Issue 50, 2004, Pages 9171-9175

  Van Otterlo, Willem A L ^a   Morgans, Garreth L ^a   Khanye, Setshaba D ^a   Aderibigbe, Blessing A A ^a   Michael, Joseph P ^a   Billing, David G ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

1,4 Benzoxazines; 1,5 Benzothiazepine; 1,6 Benzodiazocine; 1,6 Benzothiazocine; 1,6 Benzoxazocine; Benzo fused heterocycles; Isomerization; Ring closing metathesis

Indexed keywords

ANILINE DERIVATIVE; BENZOXAZINE DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL MODIFICATION; ISOMERIZATION; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY ANALYSIS;

EID: 8544258774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.108     Document Type: Article

References (46)

1. H.-G. Schmalz Angew. Chem., Int. Ed. Engl. 34 1995 1833 1836
2. R.H. Grubbs, and S. Chang Tetrahedron 54 1998 4413 4450
3. S.K. Armstrong J. Chem. Soc., Perkin. Trans. 1 1998 371 388
4. A. Furstner Angew. Chem., Int. Ed. 39 2000 3012 3043
5. A. Deiters, and S.F. Martin Chem. Rev. 104 2004 2199 2238
6. W.A.L. van Otterlo, E.L. Ngidi, E.M. Coyanis, and C.B. de Koning Tetrahedron Lett. 44 2003 311 313
7. W.A.L. van Otterlo, E.L. Ngidi, C.B. de Koning, and M.A. Fernandes Tetrahedron Lett. 45 2004 659 662
8. W.A.L. van Otterlo, E.L. Ngidi, and C.B. de Koning Tetrahedron Lett. 44 2003 6483 6486
9. W.A.L. van Otterlo, R. Pathak, and C.B. de Koning Synlett 2003 1859 1861
10. M. Arisawa, Y. Terada, M. Nakagawa, and A. Nishida Angew. Chem., Int. Ed. 41 2002 4732 4734
11. T. Nguyen Van, and N. De Kimpe Tetrahedron Lett. 45 2004 3443 3446
12. B. Schmidt Eur. J. Org. Chem. 2004 1865 1880
13. For representative examples see: T.K. Maishal, and A. Sarkar Synlett 2002 1925 1927
14. For an ene-yne RCM approach to O,O-, O,N- and N,N-8-membered benzo-fused heterocycles see: M. Mori, T. Kitamura, N. Sakakibara, and Y. Sato Org. Lett. 2 2000 543 545
15. M. Mori, T. Kitamura, and Y. Sato Synthesis 2001 654 664
16. A.J. Souers, and J.A. Ellman Tetrahedron 57 2001 7431 7448
17. L.A. Thompson, and J.A. Ellman Chem. Rev. 96 1996 555 600
18. R. Mamouni, M. Soukri, S. Lazar, M. Akssira, and G. Guillaumet Tetrahedron Lett. 45 2004 2631 2633
19. Taken from the ongoing Ph.D. project of Mr. G. L. Morgans, the ongoing M.Sc. project of Blessing A. A. Aderibigbe and the Honours project of Mr. (Rambo) S. D. Khanye
20. E. Kleinpeter, M. Gäbler, and W. Schroth Monatsh. Chem. 119 1988 233 246
21. +, 18%), 315.1 (20), 314.1 (78), 250.1 (100), 159 (98), 91.1 (57), 69.1 (34), 41.1 (20)
22. For representative examples see: I.M. Fellows, D.E. Kaelin, and S.F. Martin J. Am. Chem. Soc. 122 2000 10781 10787 and earlier references cited therein
23. H. Kishuku, M. Shindo, and K. Shishido Chem. Commun. 23 2003 350 351
24. S.J. Miller, S.-H. Kim, Z.-R. Chen, and R.H. Grubbs J. Am. Chem. Soc. 117 1995 2108 2109
25. 2 = 0.1134. CCDC-249593 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk ]
26. S. Krompiec, N. Kuźnik, R. Penczek, J. Rzepa, and J. Mrowiec-Bialoń J. Mol. Catal. A 219 2004 29 40
27. S. Krompiec, M. Pigulla, M. Krompiec, S. Baj, J. Mrowiec-Bialoń, and J. Kasperczyk Tetrahedron Lett. 45 2004 5257 5261
28. N. Kuźnik, S. Krompiec, T. Bieg, S. Baj, K. Skutil, and A. Chrobok J. Organomet. Chem. 665 2003 167 175
29. S. Krompiec, M. Pigulla, T. Bieg, W. Szczepankiewicz, N. Kuźnik, M. Krompiec, and M. Kubicki J. Mol. Catal. A 189 2002 169 185
30. S. Krompiec, M. Pigulla, W. Szczepankiewicz, T. Bieg, N. Kuźnik, K. Leszczynska-Sejda, M. Kubicki, and T. Borowiak Tetrahedron Lett. 42 2001 7095 7098
31. S. Krompiec, N. Kuźnik, T. Bieg, B. Adamus, J. Majnusz, and M. Grymel Pol. J. Chem. 74 2000 1197 1200
32. W.A.L. van Otterlo, J.-L. Panayides, and M.A. Fernandes Acta Crystallogr. E60 2004 o1586 o1588
33. M. Sridhar, B.A. Kumar, and R. Narender Tetrahedron Lett. 39 1998 2847 2850
34. +, 13%), 132.1 (100), 91.1 (8), 77 (21), 65 (7), 51 (7)
35. For a review on 1,4-benzoxazines see: M. Sainsbury (Part c)-1,4-oxazines, 1,4-benzoxazines and reduced forms M. Sainsbury Second Supplement to the 2nd Edition of Rodd's Chemistry of Carbon Compounds Heterocyclic Compounds, Pts G and H Vol. IV 1998 Elsevier Amsterdam 465 511
36. For the first published work on the RCM of enamides see: S.S. Kinderman, J.H. van Maarseveen, H.E. Schoemaker, H. Hiemstra, and F.P.J.T. Rutjes Org. Lett. 3 2001 2045 2048
37. C. Buon, L. Chacun-Lefèvre, R. Rabot, P. Bouyssou, and G. Coudert Tetrahedron 56 2000 605 614
38. Y.A. Ibrahim, H. Behbehani, and M.R. Ibrahim Tetrahedron Lett. 43 2002 4207 4210 Compound 15a has been synthesized before by Ibrahim and co-workers but our product appeared to be exclusively the Z-isomer in contrast to the 2:1 E/Z ratio described in this reference
39. For an informative review see: M.D. McReynolds, J.M. Dougherty, and P.R. Hanson Chem. Rev. 104 2004 2239 2258
40. See for example, C. Lane, and V. Snieckus Synlett 2000 1294 1296
41. A. Whitehead, J.D. Moore, and P.R. Hanson Tetrahedron Lett. 44 2003 4275 4277
42. M. Uchida, K. Otsubo, J. Matsubara, T. Ohtani, S. Morita, and K. Yamasaki Chem. Pharm. Bull. 43 1995 693 698
43. +, 9%), 256 (35), 243 (15), 220 (22), 185 (16), 129 (31), 83 (40), 69 (88), 41 (100)
44. +, 6%), 285 (38), 221 (23), 194 (18), 155 (5), 130 (100), 91 (30), 65 (11), 39 (8)
45. For reviews on 1,5-benzothiazepines see: A. Levai J. Heterocycl. Chem. 37 2000 199 214
46. A. Chimirri, R. Gitto, S. Grasso, A.M. Monforte, and M. Zappala Adv. Heterocycl. Chem. 63 1995 62 101