Preparation of peri-annulated indoles from polynitro compounds

Tetrahedron

Volumn 65, Issue 34, 2009, Pages 6868-6872

  Samet, Alexander V ^a   Yamskov, Alexei N ^a   Strelenko, Yuri A ^a   Semenov, Victor V ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHYDROBENZ[6,7]OXEPINO[4,3,2 CD]INDOLE; 2,11 DIHYDROBENZ[6,7]OXEPINO[4,3,2 CD]INDOLE; 4,6 DINITRO 1 TOSYLINDOLINE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; NITRO DERIVATIVE; OXEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CYCLIZATION; ISOMER; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 67650717992     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.074     Document Type: Article

References (34)

1. Gribble G.W. Pyrroles and their Benzo Derivatives: Applications. In: Katritzky A.R., Rees C.W., and Scriven E.F. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 2 (1996), Pergamon, New York, NY 207
2. Sundberg R.J. Pyrroles and their Benzo Derivatives: (iii) Synthesis and Applications. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 4 (1984), Pergamon, Oxford 313
3. Brown L.E., and Konopelski J.P. Org. Prep. Proced. Int. 40 (2008) 411
4. May J.A., and Stoltz B. Tetrahedron 62 (2006) 5262
5. Yamada F., Makita Y., Suzuki T., and Somei M. Chem. Pharm. Bull. 33 (1985) 2162
6. Kozlovskii A.G., Soloveva T.F., Sakharovskii V.G., and Adanin V.M. Dokl. Akad. Nauk SSSR 260 (1981) 230
7. Ku J., Jeong B., Jew S., and Park H. J. Org. Chem. 72 (2007) 8115
8. Yokoyama Y., Hikawa H., Mitsuhashi M., Uyama A., Hiroki Y., and Murakami Y. Eur. J. Org. Chem. 6 (2004) 1244
9. Kozikowski A.P., and Greco M.N. J. Org. Chem. 49 (1984) 2310
10. Yamskov A.N., Samet A.V., and Semenov V.V. Mendeleev Commun. 18 (2008) 320
11. Samet A.V., Kislyi K.A., Marshalkin V.N., Strelenko Y.A., Raihstat M.M., Nelyubina Y.V., and Semenov V.V. Tetrahedron 64 (2008) 11763
12. Kislyi K.A., Samet A.V., Strelenko Y.A., and Semenov V.V. J. Org. Chem. 73 (2008) 2285
13. 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
14. Samet A.V., K{cyrillic}islyi K.A., Marshalkin V.N., Strelenko Y.A., Nelyubina Yu.V., Lyssenko K.A., and Semenov V.V. Russ. Chem. Bull. 56 (2007) 2089
15. 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
16. Samet A.V., Zakharov E.P., Semenov V.V., Gakh A.A., and Buchanan III A.C. Synth. Commun. 31 (2001) 1441
17. Compound 1 has already been used for the preparation of biologically active indoles:. 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
18. Some alternative approaches to peri-annulated heterocyclic systems starting from polynitroaromatic compounds are described in:
19. Bastrakov M.A., Starosotnikov A.M., Kachala V.V., Nesterova E.N., and Shevelev S.A. Russ. Chem. Bull. 56 (2007) 1603
20. Zlotin S.G., Kislitsin P.G., Kucherov F.A., and Gakh A.A. Heterocycles 68 (2006) 1109
21. Kozikowski A.P., Greco M.N., and Springer J.P. J. Am. Chem. Soc. 104 (1982) 7622
22. Yamskov A.N., Samet A.V., and Semenov V.V. Russ. Chem. Bull. 52 (2003) 759
23. For a similar reaction of 2,3-dihydro-2-methyl-4,6-dinitrobenzo[b]furan, see: TNT itself reacts with 2-hydroxybenzaldehydes in a similar way to afford 1,3-dinitrodibenz[b,f]oxepines:. Hoyer H., and Vogel M. Monatsh. Chem. 93 (1962) 766
24. Yamskov A.N., Samet A.V., and Semenov V.V. Chem. Heterocycl. Compd. 41 (2005) 796
25. Murphy J.A., Khan T.A., Zhou S.-Z., Thomson D.W., and Mahesh M. Angew. Chem., Int. Ed. 44 (2005) 1356
26. Bergman J., Janosik T., Koch E., and Pelcman B. J. Chem. Soc., Perkin Trans. 1 (2000) 2615
27. Tietze L.F., and Grote T. J. Org. Chem. 59 (1994) 192
28. Suarez-Castillo O.R., Contreras-Martinez Y.M.A., Beiza-Granados L., Melendez-Rodriguez M., Villagomez-Ibarra J.R., Torres-Valencia J.M., Morales-Rios M.S., and Joseph-Nathan P. Tetrahedron 61 (2005) 8809
29. Kawasaki T., Nonaka Y., Watanabe K., Ogawa A., Higuchi K., Terashima R., Masuda K., and Sakamoto M. J. Org. Chem. 66 (2001) 1200
30. Morales-Rios M.S., Bucio M.A., and Joseph-Nathan P. Tetrahedron 52 (1996) 5339
31. Tidwell J.H., Peat A.J., and Buchwald S.L. J. Org. Chem. 59 (1994) 7164
32. Jones R.A. Pyrroles and their Benzo Derivatives: (ii) Reactivity. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 4 (1984), Pergamon, Oxford 201
33. For a large-scale synthesis with TNT, see:. Organic Syntheses Collect. Vol. I, p. 543 (1941), Wiley & Sons, New York, NY (no special safety precautions were recommended by the submitters or checkers of this procedure).
34. Moreover, TNT was successfully used for industrial production of phloroglucinol:. Castens M.L., and Kaplan J.F. Ind. Eng. Chem. 42 (1950) 402