A novel alkyne-induced recyclization of 4-hydroxymethyl or 4-formyl-1H-2,3-dihydroisoindoles-an effective pathway to substituted isobenzofurans

Tetrahedron Letters

Volumn 50, Issue 34, 2009, Pages 4851-4853

  Voskressensky, Leonid G ^a   Kulikova, Larisa N ^a   Kleimenov, Alexey ^a   Guranova, Natalia ^a   Borisova, Tatiana N ^a   Varlamov, Alexey V ^a  

^a PEOPLES FRIENDSHIP UNIVERSITY OF RUSSIA   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

4 FORMYL 1H 2,3 DIHYDROISOINDOLE DERIVATIVE; ALKYNE DERIVATIVE; ISOBENZOFURAN DERIVATIVE; ISOINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 67649833814     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.036     Document Type: Article

References (23)

1. Hafner K. Angew. Chem. 76 (1963) 1041-1050
2. Dimroth O. Ann. 364 (1909) 183
3. Itaya T., Hozumi Y., Kanai T., and Ohta T. Tetrahedron Lett. 39 (1998) 4695-4696
4. Volkova N.N., Tarasov E.V., Van Meervelt L., Toppet S., Dehaen W., and Bakulev V.A. J. Chem. Soc., Perkin Trans. 1 (2002) 1574-1580
5. Boulton J.A., Katritzky A.R., and Majid-Hamid A. J. Chem. Soc. (C) (1967) 2005-2012
6. Katritzky A.R., and Gordeev M.F. Heterocycles 35 (1993) 483-486
7. Rauhut G. J. Org. Chem. 66 (2001) 5444-5448
8. For mechanistic studies on azole-to-azole interconversion reactions of the Boulton-Katritzky type, see:. Cosimelli B., Guernelli S., Spinelli D., Buscemi S., Frenna V., and Macaluso G. J. Org. Chem. 66 (2001) 6124-6129 and references cited therein
9. Kost A.N., Sagitullin R.S., and Gromov S.P. Heterocycles 7 (1977) 997-1001
10. For example, see:. Maiboroda D.A., and Babaev E.V. Chem. Heterocycl. Compd. 31 (1995) 1251-1279
11. Litvinov V.P. Russ. Chem. Rev. 68 (1999) 39-53
12. Voskressensky L.G., Borisova T.N., Kulikova L.N., Varlamov A.V., Catto M., Altomare C., and Carotti A. Eur. J. Org. Chem. (2004) 3128-3135
13. Voskressensky L.G., Borisova T.N., Kostenev I.S., Kulikova L.N., and Varlamov A.V. Tetrahedron Lett. 47 (2006) 999-1001
14. Voskressensky L.G., Borisova T.N., Kostenev I.S., Vorobiev I.V., and Varlamov A.V. Tetrahedron Lett. 46 (2005) 1975-1979
15. Voskressensky L.G., Listratova A.V., Borisova T.N., Alexandrov G.G., and Varlamov A.V. Eur. J. Org. Chem. (2007) 6106-6117
16. Voskressensky L.G., Akbulatov S.V., Borisova T.N., and Varlamov A.V. Tetrahedron 62 (2006) 12392-12397
17. Varlamov A.V., Boltukhina E.V., Zubkov F.I., Sidorenko N.V., Chernyshev A.I., and Grudinin D.G. Chem. Heterocycl. Compd. 40 (2004) 27-33
18. Voskressensky L.G., Vorobiev I.V., Borisova T.N., and Varlamov A.V. J. Org. Chem. 73 (2008) 4596-4601
19. 2 with ethyl acetate as eluent to give isobenzofurans 11-25.
20. 3 (275.34): C, 69.79; H, 7.69; N, 5.09. Found: C, 69.83; H, 7.64; N, 5.14.
21. Gevorkyan A.R., Chukhadzhyan E.O., Chukhadzhyan El.O., and Panosyan G.A. Chem. Heterocycl Compd. 40 (2004) 177-181
22. 5 (335.17): C, 64.46; H, 7.51; N, 4.18. Found: C, 64.87; H, 7.13; N, 4.25.
23. 5 (319.14): C, 63.94; H, 6.63; N, 4.39. Found: C, 64.35; H, 6.25; N, 4.47.