Pd/C-mediated synthesis of (Z)-3-alkylidenephthalides of potential pharmacological interest

The coupling of o-bromobenzoic acid with terminal alkynes using 10% Pd/C–Et3N–CuI–PPh3 as a catalyst system leads to the synthesis of (Z)-3-alkylidenephthalides as the major product along with the traces of isocoumarin when the reaction was performed in 1,4-dioxane. The methodology afforded a range...

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Bibliographic Details
Published inTetrahedron letters Vol. 54; no. 23; pp. 2989 - 2995
Main Authors Rambabu, D., Kumar, G. Pavan, Kumar, Barange Deepak, Kapavarapu, Ravikumar, Rao, M.V. Basaveswara, Pal, Manojit
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.06.2013
Elsevier
Subjects
3-Alkylidenephthalides
Alkynes
Catalysts
Chemistry
Chemistry, Organic
Coupling
Joining
Methodology
Palladium
Pd/C
Physical Sciences
Science & Technology
Synthesis (chemistry)
Terminals
Tetrahedrons
Coupling
Pd/C
Alkynes
3-Alkylidenephthalides
3-SUBSTITUTED ISOCOUMARINS
TERMINAL ALKYNES
COX-2 INHIBITOR
GAMMA-ALKYLIDENEBUTENOLIDES
O-IODOBENZOIC ACID
INTRAMOLECULAR CYCLIZATION
SELECTIVE CYCLOOXYGENASE-2 INHIBITORS
(Z)-2-EN-4-YNOIC ACIDS
PALLADIUM-CATALYZED HETEROANNULATION
OXIDATIVE CYCLIZATION
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Summary:The coupling of o-bromobenzoic acid with terminal alkynes using 10% Pd/C–Et3N–CuI–PPh3 as a catalyst system leads to the synthesis of (Z)-3-alkylidenephthalides as the major product along with the traces of isocoumarin when the reaction was performed in 1,4-dioxane. The methodology afforded a range of compounds including (Z)-3-(4-(methylsulfonyl)benzylidene)isobenzofuran-1(3H)-one of potential pharmacological interest.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1359-8562
1873-3581
DOI:10.1016/j.tetlet.2013.03.121