A straightforward preparation of benzo[f]naphtho[b][1,4]oxazepines from TNT

Tetrahedron

Volumn 64, Issue 51, 2008, Pages 11763-11767

  Samet, Alexander V ^a   Kislyi, Konstantine A ^a   Marshalkin, Victor N ^a   Strelenko, Yuri A ^a   Raihstat, Mikhail M ^a   Nelyubina, Yulia V ^b   Semenov, Victor V ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

1 Nitroso 2 naphthol; 2,4,6 Trinitrotoluene; Benzo f naphtho b 1,4 oxazepines; SNAr reactions

Indexed keywords

NAPHTHOL DERIVATIVE; NITRO DERIVATIVE; OXAZEPINE DERIVATIVE; TRINITROTOLUENE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; SUBSTITUTION REACTION; X RAY DIFFRACTION;

EID: 55549105386     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.090     Document Type: Article

References (21)

1. See, for example:
2. Pullagurla M., Siripurapu U., Kolanos R., Bondarev M.L., Dukat M., Setola V., Roth B.L., and Glennon R.A. Bioorg. Med. Chem. Lett. 15 (2005) 5298
3. Samet A.V., Zakharov E.P., Semenov V.V., Gakh A.A., and Buchanan III A.C. Synth. Commun. 31 (2001) 1441
4. Zlotin S.G., Kislitsin P.G., Podgursky A.I., Samet A.V., Semenov V.V., Buchanan III A.C., and Gakh A.A. J. Org. Chem. 65 (2000) 8439
5. Zlotin S.G., Kislitsin P.G., Kucherov F.A., Serebryakov E.A., Strelenko Y.A., and Gakh A.A. Heterocycles 68 (2006) 2483
6. Kislyi K.A., Samet A.V., and Semenov V.V. Russ. J. Org. Chem. 42 (2006) 292
7. Kislyi K.A., Samet A.V., Strelenko Y.A., and Semenov V.V. J. Org. Chem. 73 (2008) 2285
8. Samet A.V., Marshalkin V.N., Kislyi K.A., Chernysheva N.B., Strelenko Y.A., and Semenov V.V. J. Org. Chem. 70 (2005) 9371
9. Samet A.V., Kislyi K.A., Marshalkin V.N., Strelenko Y.A., NelyubinaYu V., Lyssenko K.A., and Semenov V.V. Russ. Chem. Bull. 56 (2007) 2089
10. Zlotin S.G., Kislitsin P.G., Samet A.V., Serebryakov E.A., Konyushkin L.D., Semenov V.V., Buchanan III A.C., and Gakh A.A. J. Org. Chem. 65 (2000) 8430
11. For an alternative approach to benzo[f]naphtho[b][1,4]oxazepines and biological studies, see:. Nagarajan K., David J., Kulkarni Y.S., Hendi S.B., Shenoy S.J., and Upadhyaya P. Eur. J. Med. Chem.-Chim. Ther. 21 (1986) 21
12. Chernysheva N.B., Samet A.V., Marshalkin V.N., Polukeev V.A., and Semenov V.V. Mendeleev Commun. (2001) 109
13. - failed to displace nitro groups in TNT:. Shevelev S.A., Dutov M.D., and Serushkina O.V. Russ. Chem. Bull. 44 (1995) 2424
14. Sachs F., and Kempf R. Chem. Ber. 35 (1902) 1224
15. Sharp J.T. Seven-membered Rings with Two or More Heteroatoms. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 7 (1984), Pergamon, Oxford 630
16. This approach is somewhat similar to a known synthesis of dibenz[b,f]oxepines from TNT and 2-hydroxybenzaldehydes:. Hoyer H., and Vogel M. Monatsh. Chem. 93 (1962) 766
17. Fischer W., and Kvita V. Helv. Chim. Acta 68 (1985) 846
18. Shevelev S.A., Dalinger I.L., and Cherkasova T.I. Tetrahedron Lett. 42 (2001) 8539
19. Vinogradov V.M., Dalinger I.L., Starosotnikov A.M., and Shevelev S.A. Russ. Chem. Bull. 50 (2001) 464
20. Starosotnikov A.M., Kachala V.V., Lobach A.V., Vinogradov V.M., and Shevelev S.A. Russ. Chem. Bull. 52 (2003) 1782
21. Vorob'ev S.S., Dutov M.D., Vatsadze I.A., Petrosyan E.P., Kachala V.V., Strelenko Y.A., and Shevelev S.A. Russ. Chem. Bull. 56 (2007) 1020