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Volumn , Issue 9, 2008, Pages 1309-1312

Intramolecular Friedel-Crafts reaction of indoles with carbonyl groups: A simple synthesis of 3- and 4-substituted β-carbolin-1-ones

(3) Cincinelli, Raffaella a Dallavalle, Sabrina a Merlini, Lucio a

a UNIVERSITY OF MILAN (Italy)

Author keywords

carbolinones; Friedel Crafts reaction; Heterocycles; Indoles; Ring closure

Indexed keywords

BETA CARBOLINE; CARBONYL DERIVATIVE; INDOLE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; FRIEDEL CRAFTS REACTION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 45849114019 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072613 Document Type: Article

Times cited : (17)

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- General Procedure for the Synthesis of Hydroxyamides 3 and 7: The appropriate amino alcohol 2 (3 mmol) was dissolved in anhyd THF (12 mL) and then EDC (3 mmol, HOBt (3 mmol) and the corresponding indole-2-carboxylic acid (2 mmol) were added sequentially at 25°C. After stirring overnight at r.t, evaporating the solvent, pouring the product into sat. aq NaHCO 3, extracting with EtOAc, washing with 1 N HCl, sat. aq NaHCO 3, brine, drying over Na2SO4 and concentrating the combined extract gave the amide. General Procedure for the Synthesis of Ketoamides 4a,e,g, and 8c: A suspension of the appropriate amide 3 or 7c (0.45 mmol) in EtOAc (6 mL) was added with IBX (1.35 mmol, then immersed in an oil bath set to 80°C and stirred vigorously open to the atmosphere. After 2.5 h (TLC monitoring) the reaction was cooled to r.t. and filtered through a medium glass frit. The filter cake was washed with EtOAc-CH
- 6): δ = 7.51 (d, J = 8.9 Hz, 1 H), 7.38 (d, J = 8.6 Hz, 2 H), 7.11 (dd, J = 2.6, 8.9 Hz, 1 H), 7.02 (d, J = 8.6 Hz, 2 H), 6.91 (s, 1 H), 6.86 (d, J = 2.6 Hz, 1 H)

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