Synthesis and isomerization of N-α-aza-heteroaryl-β-lactams

Tetrahedron

Volumn 62, Issue 51, 2006, Pages 12064-12070

  Troisi, Luigino ^a   Ronzini, Ludovico ^a   Granito, Catia ^a   Pindinelli, Emanuela ^a   Troisi, Alessandro ^b   Pilati, Tullio ^c  

^a UNIVERSITY OF SALENTO   (Italy)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c CNR   (Italy)

Author keywords

Lactams; Carbonylative cycloaddition; Isomerization; Pyrimidinones

Indexed keywords

(4 METHYLTHIAZOL 2 YLMETHYLENE)PYRIDIN 2 YLAMINE; (4 METHYLTHIAZOL 2 YLMETHYLENE)THIAZOL 2 YLAMINE; 1 BENZOTHIAZOL 2 YL 3 ETHYLIDENE 4 PHENYLAZETIDIN 2 ONE; 2 BENZOTHIAZOL 2 YL 3 ETHYLPYRIDO[1,2 A]PYRIMIDIN 4 ONE; 2 BENZOTHIAZOL 2 YL 3 ETHYLTHIAZOLO[3,2 A]PYRIMIDIN 4 ONE; 3 ETHYL 2 (4 METHYLTHIAZOL 2 YL)THIAZOLO[3,2 A]PYRIMIDIN 4 ONE; 3 ETHYLIDENE 4 (4 METHYLTHIAZOL 2 YL) 1 PYRIDIN 2 YLAZETIDIN 2 ONE; 3 ETHYLIDENE 4 PHENYL 1 THIAZOL 2 YLAZETIDIN 2 ONE; 4 BENZOTHIAZOL 2 YL 3 ETHYLIDENE 1 PYRIDIN 3 YLAZETIDIN 2 ONE; BENZOTHIAZOL 2 YL BENZYLIDENE AMINE; BENZOTHIAZOL 2 YLMETHYLENEPYRIDIN 2 YLAMINE; BENZOTHIAZOL 2 YLMETHYLENEPYRIDIN 3 YLAMINE; BENZOTHIAZOL 2 YLMETHYLENETHIAZOL 2 YLAMINE; BENZYLIDENE THIAZOL 2 YL AMINE; BETA LACTAM DERIVATIVE; N THIAZOL 2 YL 2 BENZYLIDENEBUT 3 ENAMIDE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; ISOMERIZATION; PRIORITY JOURNAL;

EID: 33750727980     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.075     Document Type: Article

References (32)

1. Singh G.S. Mini Rev. Med. Chem. 4 (2004) 69-92
2. Banik F., Beker F., and Banik B.K. J. Med. Chem. 46 (2003) 12-15
3. Zhou N.E., Guo D., Thomas G., Reddy A.V.N., Kaleta J., Purisima E., Menard R., Micetich R.G., and Singh R. Bioorg. Med. Chem. Lett. 13 (2003) 139-141
4. Krause B.R., Sliskovic D.R., and Bocan T.M.A. Expert Opin. Investig. Drugs 4 (1995) 353
5. Alcaide B., and Almendros P. Synlett (2002) 381-393
6. Parsons P.J., Camp N.P., Underwood J.M., and Harvey D.M. J. Chem. Soc., Chem. Commun. (1995) 1461-1462
7. Wasserman H.H., and Matsuyama H. J. Am. Chem. Soc. 103 (1981) 461-462
8. Banik B.K., Manhas M.S., and Bose A.K. J. Org. Chem. 59 (1994) 4714-4716
9. Manhas M.S., Hedge V.R., Wagle D.R., and Bose A.K. J. Chem. Soc., Perkin Trans. 1 (1985) 2045-2050
10. Thomas E.J., and Williams A.C. J. Chem. Soc., Perkin Trans. 1 (1995) 351-358
11. Baldwin J.E., Adlington R.M., Gollins D.W., and Godfrey C.R.A. Tetrahedron 51 (1995) 5169-5180
12. Van Hove F., Vanwetswinkel S., Marchand-Brynaert J., and Fastrez J. Tetrahedron Lett. 36 (1995) 9313-9316
13. Baldwin J.E., Adlington R.M., Elend A.S., and Smith M.L. Tetrahedron 51 (1995) 11581-11594
14. Xiaobing L., Chuansheng N., and Miller M.J. Tetrahedron Lett. 36 (1995) 1617-1620
15. Troisi L., De Vitis L., Granito C., and Epifani E. Eur. J. Org. Chem. (2004) 1357-1362
16. Troisi L., Ronzini L., Granito C., De Vitis L., and Pindinelli E. Tetrahedron 62 (2006) 1564-1574
17. Troisi L., Granito C., and Pindinelli E. In: Attanasi O.A., and Spinelli D. (Eds). Target in Heterocyclic System, Chemistry and Properties Vol. 8 (2005), Italian Society of Chemistry, Rome 187-215
18. Taguchi K., and Westheimer F.H. J. Org. Chem. 36 (1971) 1570-1572
19. Dyer J.R. Application of Absorption Spectroscopy of Organic Compounds (1965), Prentice-Hall, Englewood Cliffs, NJ 78-79
20. Crandall J.K., Arrington J.P., and Hen J. J. Am. Chem. Soc. 22 (1967) 6208-6213
21. Cardillo G., Fabbroni S., Gentilucci L., Pierciaccante R., and Tolomelli A. Arkivok VI (2005) 136-152
22. 1H FT NMR Spectra Vol. I (1993), Aldrich Chemical, USA
23. Crystallographic data (excluding structure factors) for the structures 14 and 18 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 607028 and CCDC 607027. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
24. Alcaide B., Dominguez G., Martìn-Domenech A., Plumet J., Monge A., and Pèrez-Garcìa V. Heterocycles 26 (1987) 1461
25. Micetich R.G., Maiti S.N., Tanaka M., Yamazaki T., and Ogawa K. J. Org. Chem. 51 (1986) 853-858
26. Alajarìn M., and Sànchez-Andrada S. J. Org. Chem. 66 (2001) 8470-8477
27. Nguyen M., Ha T., and More O'Ferral R.A. J. Org. Chem. 55 (1990) 3251-3256
28. Alcaide B., Aly M., Rodriguez C., and Rodriguez-Vicente A. J. Org. Chem. 65 (2000) 3453-3459
29. Zanatta N., Barichello R., Bonacorso H.G., and Martins M.A.P. Synthesis 5 (1999) 765-768
30. Olofson R.A., Vander Meer R.K., Hoskin D.H., Bernheim M.Y., Stournas S., and Morrison D.S. J. Org. Chem. 49 (1984) 3367-3372
31. D=-1139.700231 (-1139.877497).
32. Alajarìn M., Vidal A., Sánchez-Andrada P., Tovar F., and Ochoa G. Org. Lett. 2 (2000) 965-968