An efficient ZnO-catalyzed synthesis of novel indole-annulated thiopyrano-chromene derivatives via Domino Knoevenagel-hetero-Diels–Alder reaction

An efficient synthesis of pentacyclic indole derivatives is achieved via domino Knoevenagel-hetero-Diels–Alder reactions of indolin-2-thiones and O-propargylated salicylaldehyde derivatives in CH 3CN in the presence of 10 mol % of ZnO as a heterogeneous catalyst. The products are formed in good to e...

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Bibliographic Details
Published inTetrahedron letters Vol. 50; no. 48; pp. 6723 - 6727
Main Authors Kiamehr, Mostafa, Moghaddam, Firouz Matloubi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.12.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Hetero-Diels–Alder reaction
Indolin-2-thione
Knoevenagel reaction
O-propargylated salicylaldehyde
Physical Sciences
Science & Technology
ZnO
Hetero-Diels–Alder reaction
Indolin-2-thione
O-propargylated salicylaldehyde
ZnO
Knoevenagel reaction
NATURAL-PRODUCTS
ZINC-OXIDE
RING-SYSTEM
REARRANGEMENT
SOLVENT-FREE
KF-AL2O3
FUSED INDOLES
CYCLOADDITIONS
REGIOSELECTIVE SYNTHESIS
Hetero-Diels-Alder reaction
THIOPHENES
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Summary:An efficient synthesis of pentacyclic indole derivatives is achieved via domino Knoevenagel-hetero-Diels–Alder reactions of indolin-2-thiones and O-propargylated salicylaldehyde derivatives in CH 3CN in the presence of 10 mol % of ZnO as a heterogeneous catalyst. The products are formed in good to excellent yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.09.106