Synthesis of novel fused azecine ring systems through application of the tert-amino effect

Tetrahedron

Volumn 66, Issue 13, 2010, Pages 2331-2339

  Dunkel, Petra ^a   Túrós, György ^a   Bényei, Attila ^b   Ludányi, Krisztina ^a   Mátyus, Péter ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Fused azecine ring systems; Microwave; Regioselective Suzuki coupling; tert Amino effect

Indexed keywords

ALDEHYDE DERIVATIVE; BIPHENYL DERIVATIVE; BORONIC ACID DERIVATIVE; PYRIDAZINE DERIVATIVE; TERPHENYL DERIVATIVE;

ARTICLE; ISOMERIZATION; KNOEVENAGEL CONDENSATION; PRIORITY JOURNAL; RING CLOSING METATHESIS; SUZUKI REACTION; SYNTHESIS;

EID: 77349092323     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.02.014     Document Type: Article

References (44)

1. Aladesanmi A.J., Kelley C.J., and Leary J.D. J. Nat. Prod. 46 (1983) 127-131
2. McDonald E., and Suksamrarn A. Tetrahedron Lett. 49 (1975) 4425-4428
3. Marino J.P., and Samanen J.M. J. Org. Chem. 41 (1976) 179-180
4. McDonald E., and Suksamrarn A. J. Chem. Soc., Perkin Trans. 1 5 (1978) 434-440
5. Efferth T., Sauerbrey A., Halatsch M.-E., Ross D.D., and Gebhart E. Naunyn-Schmiedeberg's Arch. Pharmacol. 367 (2003) 56-67
6. Hart J.B., Mason J.M., and Gerard P.J. Tetrahedron 57 (2001) 10033-10038
7. Kulkarni B.K., Dhar R.K., and de Souza N.J. J. Heterocycl. Chem. 27 (1990) 623-626
8. Xiao X., Liu J., Hu J., Zhu X., Yang H., Wang C., and Zhang Y. Eur. J. Pharmacol. 591 (2008) 21-27
9. Saeed S.A., Gilani A.H., Majoo R.U., and Shah B.H. Pharmacol. Res. 36 (1997) 1-7
10. Sawa, Y.; Hirose, K.; Maeda, S.; Hamada, Y. U.S. Patent 3,932,384, 1976;
11. Chem. Abstr. 80 (1976) 146050
12. Kassack M.U., Höfgen B., Decker M., Eckstein N., and Lehmann J. Naunyn-Schmiedeberg's Arch. Pharmacol 366 (2002) 543-550
13. Mohr P., Decker M., Enzensperger C., and Lehmann J. J. Med. Chem. 49 (2006) 2110-2116
14. Meth-Cohn O., and Suschitzky H. Adv. Heterocycl. Chem. 14 (1972) 211-278
15. Quintela J.M. Recent Res. Dev. Org. Chem. 7 (2003) 259-278
16. Verboom W., and Reinhoudt D.N. Recl. Trav. Chim. Pays-Bas 109 (1990) 311-324
17. Mátyus P., Éliás O., Tapolcsányi P., Polonka-Bálint A., and Halász-Dajka B. Synthesis 16 (2006) 2625-2639
18. Polonka-Bálint A., Saraceno C., Ludányi K., Bényei A., and Mátyus P. Synlett (2008) 2846-2850
19. Földi, Á. A.; Mátyus, P., unpublished results.
20. Buchwald, S. L.; Huang, X.; Zim, D. WO 2004052939;
21. Chem. Abstr. 141 (2004) 71718
22. Bonnaventure I., and Charette A.B. J. Org. Chem. 73 (2008) 6330-6340
23. Krajsovszky G., Károlyházy L., Riedl Zs., Csámpai A., Dunkel P., Lernyei A., Dajka-Halász B., Hajós Gy., and Mátyus P. J. Mol. Struct. (THEOCHEM) 713 (2005) 235-243
24. Beška E., and Rapoš P. J. Chem. Soc., Perkin Trans. 1 (1976) 2470-2471
25. Haider N., and Wobus A. Heterocycles 68 (2006) 2549-2561
26. Stevenson T.M., Crouse B.A., Thieu T.V., Gebreysus C., Finkelstein B.L., Sethuraman M.R., Dubas-Cordery C.M., and Piotrowski D.L. J. Heterocycl. Chem. 42 (2005) 427-435
27. Lauer M., and Wulff G. J. Organomet. Chem. 256 (1983) 1-9
28. Howard, H. R. EP 0957099;
29. Chem. Abstr. 131 (1999) 351348
30. Biadatti, T.; Dumais, L.; Soulet, C.; Talano, S.; Daver, S. WO 2006066978;
31. Chem. Abstr. 145 (2006) 103438
32. Verboom W., Reinhoudt D.N., Visser R., and Harkema S. J. Org. Chem. 49 (1984) 269-276
33. Ju Y., and Varma R.S. J. Org. Chem. 71 (2006) 135-141
34. Kaval N., Dehaen W., Mátyus P., and Van der Eycken E. Green Chem. 6 (2004) 125-127
35. Kaval N., Halász-Dajka B., Vo-Thanh G., Dehaen W., Van der Eycken J., Mátyus P., Loupy A., and Van der Eycken E. Tetrahedron 61 (2005) 9052-9057
36. The X-ray data are available from the Cambridge Crystallographic Data Centre CCDC under the numbers 731714-731718 for 12a, 18a, 19a, 20a and 21c, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk. The details of the X-ray structures will be published elsewhere.
37. O'Leary J., Formosa X., Skranc W., and Wallis J.D. Org. Biomol. Chem. 3 (2005) 3273-3283
38. Guven A., and Jones R.A. J. Chem. Res., Miniprint 9 (1993) 2411-2428
39. Mongevega A., Palop J.A., Martinez M.T., and Fernandez-Alvarez E. An. Quim. 75 (1979) 889
40. Ali M.I., El-Sayed A.A., Abdel-Fattah A.M., and El-Reedy A.M. Indian J. Chem. B 15 (1977) 64-66
41. Gait S.F., Peek M.E., Rees C.W., and Storr R.C. J. Chem. Soc., Perkin Trans. 1 (1974) 1248-1260
42. Mascarelli G. Gazz. Chim. Ital. 61 (1931) 782-788
43. Fuhrer W., and Gschwend H.W. J. Org. Chem. 44 (1979) 1133-1136
44. Rocca P., Marsais F., Godard A., and Queguiner G. Tetrahedron 49 (1993) 49-64