Journal
GREEN CHEMISTRY
Volume 14, Issue 3, Pages 750-757Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2gc16517a
Keywords
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Funding
- Department of Science and Technology, New Delhi
- MICINN, Spain [DST/INT/SPAIN/09, ACI2009-0956, CTQ2009-12320-BQU]
- King Saud University [RGP-VPP-026]
- DST under IRHPA
- Council of Scientific and Industrial Research, New Delhi
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A library of trans-5-aroyl-2-(indol-3-yl)-4-aryl-4,5-dihydrofuran-3-carbonitriles was diastereoselectively synthesized in excellent yields from the reaction of 2-(3-indolylcarbonyl)-3-aryl-2-propenenitriles with (2-aryl-2-oxoethyl)pyridinium bromides in the presence of triethylamine via a simple, user-friendly domino process carried out in water. Extraction and chromatographic steps were avoided, since the final products could be simply filtered from the aqueous reaction medium and recrystallized. This one-pot transformation generates one C C and one C O bond and presumably proceeds by a domino sequence involving the generation of a pyridinium ylide, a Michael addition and a final annulation via intramolecular nucleophilic substitution.
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