Furan as a 1,3-diketone equivalent: the second type furan recyclization applied to indole synthesis

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4113-4116

  Butin, Alexander V ^a  

^a KUBAN STATE TECHNOLOGICAL UNIVERSITY   (Russian Federation)

Author keywords

Furan; Indole; Recyclization

Indexed keywords

1,3 DIKETONE; FURAN; INDOLE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PHASE TRANSITION; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33646529930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.080     Document Type: Article

References (26)

1. See the following review:. Butin A.V., and Abaev V.T. Izvest. AN. Seriya Khim. (2001) 1436-1443
2. Butin A.V., Krapivin G.D., Zavodnik V.E., and Kul'nevich V.G. Khim. Geterotsikl. Soedin. (1993) 616-626
3. Abaev V.T., Gutnov A.V., and Butin A.V. Khim. Geterotsikl. Soedin. (1998) 603-607
4. Gutnov A.V., Butin A.V., Abaev V.T., Krapivin G.D., and Zavodnik V.E. Molecules 4 (1999) 204-218
5. See the following review:. Butin A.V., Gutnov A.V., Abaev V.T., and Krapivin G.D. Molecules 4 (1999) 52-61
6. Butin A.V., Stroganova T.A., Lodina I.V., and Krapivin G.D. Tetrahedron Lett. 42 (2001) 2031-2033
7. Gutnov A.V., Abaev V.T., Butin A.V., and Dmitriev A.S. J. Org. Chem. 66 (2001) 8685-8686
8. Abaev V.T., Osipova A.A., and Butin A.V. Khim. Geterotsikl. Soedin. (2001) 849-850
9. Butin A.V., Abaev V.T., Mel'chin V.V., and Dmitriev A.S. Tetrahedron Lett. 46 (2005) 8439-8441
10. Takano S., Otaki S., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1983) 1172-1174
11. Haley Jr. J.F., and Keehn P.M. Tetrahedron Lett. (1973) 4017-4020
12. Bezoari M.D., and Paudler W.W. J. Org. Chem. 45 (1980) 4584-4586
13. Faragher R., and Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1 (1979) 258-262
14. Short F.W., and Rockwood G.M. J. Heterocycl. Chem. 6 (1969) 713-722
15. Vijayasarathy P.R., and Khrishna Rao G.S. Indian J. Chem. 11 (1973) 301-302
16. Popp F.D., Schleigh W.R., and Katz L.E. J. Chem. Soc. (C) (1968) 2253-2257
17. Kharchenko V.G., Markushina I.A., and Gubina T.I. Zh. Org. Khimii 18 (1982) 394-399
18. Kurihara T., Harusava S., Hirai J., and Yoneda R. J. Chem. Soc., Perkin Trans. 1 (1987) 1771-1776
19. See also the following reviews:. Dean F.M. Adv. Heterocycl. Chem. 30 (1982) 167-238
20. Dean F.M. Adv. Heterocycl. Chem. 31 (1982) 237-344
21. Piancatelli G., D'Auria M., and D'Onofrio F. Synthesis (1994) 867-889
22. 2 (8 g, 0.06 mol) in 100 ml of water. The reaction mixture was stirred for 12 h at room temperature. After completion of the reaction, the resulting precipitated product was filtered off and recrystallized from ethanol/acetone mixture. Yields of 5-arylfurfurals 1a-d were 45-53%. The yield of 2-acetyl-5-phenylfuran 1e was 41%.
23. Compounds 2 were synthesized according to the procedure reported earlier:. Ono A., Suzuki N., and Kamimura J. Synthesis (1987) 736-738 A typical procedure is as follows: To a stirred and cooled solution (0-5 °C) of aldehyde 1a in tetrahydrofuran (8.68 g, 0.04 mol), anhydrous aluminum chloride (9.58 g, 0.072 mol) and sodium borohydride (2.74 g, 0.072 mol) were added portionwise and the resulting suspension was stirred at 0-5 °C for 20 min and then brought to reflux. After 1-2 h (TLC monitoring) the reaction mixture was cooled and poured into 700 ml of water. The product was extracted with ether (3 × 50 ml) and the combined ethereal extract was dried over sodium sulfate, treated with active charcoal and evaporated under reduced pressure. The obtained residue 2a was used in the next step as such
24. A typical procedure is as follows: To an ethanolic solution of compound 2a (8.12 g, 0.04 mol) active Raney nickel was added (4 g) along with 10 ml of hydrazine hydrate and the reaction mixture refluxed for 1-2 h. After completion of the reaction (TLC monitoring) the nickel was filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in benzene/hexane mixture (1:1) and filtered through a pad of silica gel and evaporated under reduced pressure. The obtained residue 3a was used in the next step. Warning: Care should be taken when handling benzene as a solvent due to its carcinogenic properties.
25. Ar), 7.86 (1H, s, NH). Warning: Care should be taken when handling benzene as a solvent due to its carcinogenic properties.
26. Ar). Warning: Care should be taken when handling benzene as a solvent due to its carcinogenic properties.