Synthesis of 1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol

Tetrahedron Letters

Volumn 48, Issue 51, 2007, Pages 8972-8975

  Hernández, Eliud ^a   Vélez, Jessica M ^a   Vlaar, Cornelis P ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDRO BENZO[D][1,3]OXAZIN 2 ONE DERIVATIVE; 2 HYDROXYMETHYLBENZAMIDE; BENZENE DERIVATIVE; BENZOXAZINONE DERIVATIVE; BIS(TRIFLUOROACETOXY)IODOBENZENE; PHTHALIDE DERIVATIVE; UNCLASSIFIED DRUG;

AMINOLYSIS; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 36249014846     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.114     Document Type: Article

References (20)

1. Patel M., Ko S.S., McHugh R.J., Markwalder J.A., Srivasta A.S., Cordova B.C., Klabe R.M., Erickson-Viitanen S., Trainor G.L., and Seitz S.P. Bioorg. Med. Chem. Lett. 9 (1999) 2805-2810
2. Fensome A., Bender R., Chopra R., Cohen J., Collins M.A., Hudak V., Malakian K., Lockhead S., Olland A., Svenson K., Terefenko E.A., Unwalla R.J., Wilhelm J.M., Wolfrom S., Zhu Y., Zhang Z., Zhang P., Winneker R.C., and Wrobel J. J. Med. Chem. 48 (2005) 5092-5095
3. Kern J.C., Terefenko E.A., Fensome A., Unwalla R., Wrobel J., Zhu Y., Cohen J., Winneker R., Zhang Z., and Zhang P. Bioorg. Med. Chem. Lett. 17 (2007) 189-192
4. Pierce, M. E.; Choudhury, A.; Lawrence, R.; Radesca, L. A. U.S. Patent # 5,932,726, 1999.
5. Meyers A.I., and Mielich E.D. J. Org. Chem. 40 (1975) 3158-3159
6. Snieckus V. Heterocycles 14 (1980) 1649-1676
7. Meyers A.I., Hanagan M.A., Trefonas L.M., and Baker R.J. Tetrahedron 3 (1983) 1991-1999
8. Sibi M.P., Miah M.A.J., and Snieckus V. J. Org. Chem. 49 (1984) 737-742
9. Garibay P., Toy P.H., Hoeg-Jensen T., and Janda K.D. Synlett (1999) 1438-1440
10. Hayat S., Atta-ur-Rahman, Choudhary M.I., Khan K.M., and Bayer E. Tetrahedron Lett. 42 (2001) 1647-1649
11. Bayer E., Hayat S., Atta-ur-Rahman, Choudhary M.I., Khan K.M., Shah S.T.A., Imran-ul-Haq M., Anwar M.U., and Voelter W. Arzneimittel-Forschung-Drug Research 55 (2005) 588-597
12. Levin J.I., Turos E., and Weinreb S.M. Synth. Commun. 12 (1982) 989-993
13. Huang P.-Q., Zheng X., and Deng X.-M. Tetrahedron Lett. 42 (2001) 9039-9041
14. Hofmann A.W. Ber. 14 (1881) 2725
15. Zhdankin V.V., and Stang P. Chem. Rev. 102 (2002) 2523-2584
16. Moriarty R.M., Chany II C.J., Prakash O., and Tuladhar S.M. J. Org. Chem. 58 (1993) 2478-2482
17. Prakash O., Batra H., Kaur H., Sharma P.K., Sharma V., Singh S.P., and Moriarty R.M. Synthesis (2001) 541-543
18. Yu C., Jiang Y., Liu B., and Hu L. Tetrahedron Lett. 42 (2001) 1449-1452
19. + 152.0706, found 152.0703.
20. + 150.0550, found 150.0551.