Environmentally benign, sequential synthesis of 3,4-dihydro-2H-1,4- benzoxazines under phase transfer catalysis conditions †

Green Chemistry

Volumn 5, Issue 4, 2003, Pages 367-369

  Albanese, Domenico ^a   Donghi, Andrea ^a   Landini, Dario ^a   Lupi, Vittoria ^a   Penso, Michele ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZINE DERIVATIVE; CHLORIDE; EPOXIDE; NITROGEN DERIVATIVE; SODIUM HYDROXIDE; SULFONAMIDE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ENVIRONMENT; METHODOLOGY; PHASE TRANSITION; RING OPENING;

EID: 0042882317     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b304095j     Document Type: Article

References (16)

1. (a) A.-S. Bourlot, I. Sánchez, G. Dureng, G. Guillaumet, R. Massingham, A. Monteil, E. Winslow, M. D. Pujol and J.-Y. Mérour, J. Med. Chem., 1998, 41, 3142;
2. (b) D. W. Combs, M. S. Rampulla, S. C. Bell, D. H. Klaubert, A. J. Tobia, R. Falotico, B. Haertlein, C. Lakas-Weiss and J. B. Moore, J. Med. Chem., 1990, 33, 380;
3. (c) E. T. D'Ambra, G. K. Estep, R. M. Bell, A. M. Eissenstat, A. K. Josef, J. S. Ward, A. D. Haycock, R. E. Baizman, M. F. Casiano, C. N. Beblin, M. S. Chippari, D. J. Greo, K. R. Kullnig and T. G. Daley, J. Med. Chem., 1992, 35, 124;
4. (d) M. Largeron, H. Dupuy and M. B. Fleury, Tetrahedron, 1995, 51, 4953.
5. D. Albanese, D. Landini and M. Penso, Chem. Commun., 1999, 2095.
6. D. Albanese, D. Landini, V. Lupi and M. Penso, Adv. Synth. Catal., 2002, 344, 299.
7. D. Albanese, D. Landini, V. Lupi and M. Penso, Ind. Eng. Chem. Res., 2003, 42(4), 680.
8. The ring opening step occurs in a regioselective fashion. A noticeable amount of the regioisomer, deriving from the nucleophilic attack on the substituted side of the epoxide, was detected in the case of styrene oxide only (see ref. 4).
9. (a) Organic Synthesis in Water, ed. P. A. Grieco, Blackie Academic and Professional, London, 1998;
10. (b) C. J. Li and T. H. Chang, in Organic Reactions in Aqueous Media, Wiley, New York, 1997.
11. J. H. Clark, Chem. Rev., 1980, 80, 429.
12. I. Huertas, I. Gallardo and J. Marquet, Tetrahedron Lett., 2001, 42, 3439.
13. D. Albanese, D. Landini and M. Penso, Synthesis, 1994, 34.
14. D. Landini, A. Maia and A. Rampoldi, J. Org. Chem., 1989, 54, 328.
15. D. Albanese, D. Landini and M. Penso, J. Org. Chem., 1998, 63, 9587.
16. Y. Matsumoto, R. Tsuzuki, A. Matsuhisa, K. Takayama, W. Uchida, M. Asano, I. Yanagisawa and T. Yoden, US Patent 5420 126, 1995.