Generation and Intermolecular Reactions of 2-Indolylacyl Radicals

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1697-1700

  Bennasar, M Lluïsa ^a   Roca, Tomàs ^a   Griera, Rosa ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

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ARTICLE;

EID: 0000467967     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0100576     Document Type: Article

References (30)

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10. 3P in THF at room temperature, following the procedure reported by the following: Batty, D.; Crich, D. Synthesis 1990, 273-275.
11. 6 (6 mL). After an additional 2-3 h at reflux, the solution was concentrated under reduced pressure, and the resulting residue was chromatographed (flash, hexanes-AcOEt).
12. Casamitjana, N.; López, V.; Jorge, A.; Bosch, J.; Molins, E.; Roig, A. Tetrahedron 2000, 56, 4027-4042.
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14. 6 (12 mL). After an additional 2-3 h at reflux, the reaction was worked up as in the above Method A.
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17. (a) Joule, J. A. In Indoles, The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4; Chapter VI.
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20. 6 (30 mL) was refluxed under sun-lamp irradiation (300 W) for 24 h. The reaction was worked up as in the above Method A.
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26. For a recent application of the Minisci reaction, see: Doll, M. K.-H. J. Org. Chem. 1999, 64, 1372-1374.
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28. (b) Hasan, I.; Marinelli, E. R.; Lin, L.-C. C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157-164. Indole 3b was prepared in 74% yield by N-benzylation of 3c with benzyl bromide (1.1 equiv) and NaH (2.2 equiv) in 5:1 DMF-THF.
29. 2, AcOEt-hexanes).
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