Efficient synthesis of pentacyclic benzosultam-annulated thiopyranoindoles via domino Knoevenagel / intramolecular hetero-Diels–Alder reactions in water

A convenient catalyst-free synthesis of hitherto unknown pentacyclic benzosultam-annulated thiopyranoindole derivatives is reported which proceeds via domino Knoevenagel / intramolecular hetero-Diels–Alder reactions of ( E )- N -alkyl-2-aryl- N -(2-formylphenyl)ethene-1-sulfonamides with indoline-2-...

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Bibliographic Details
Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 56; no. 3; pp. 392 - 398
Main Authors Kiamehr, Mostafa, Khademi, Fahimeh, Jafari, Behzad, Langer, Peter
Format Journal Article
LanguageEnglish
Published New York Springer US 01.03.2020
Springer Nature
Springer
Springer Nature B.V
Subjects
Aromatic compounds
Cascade chemical reactions
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Diels-Alder reactions
Ethylene
Organic Chemistry
Pharmacy
Physical Sciences
Science & Technology
Sulfonamides
cyclizations
regioselectivity
benzosultams
thiopyranoindole
domino reactions
DESIGN
ONE-POT SYNTHESIS
NATURAL-PRODUCTS
CATALYST
THIOPYRANOCOUMARIN DERIVATIVES
FUSED INDOLES
TETRAHYDROQUINOLINES
BIOLOGICAL EVALUATION
STEREOSELECTIVE-SYNTHESIS
TRANSFORMATIONS
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Summary:A convenient catalyst-free synthesis of hitherto unknown pentacyclic benzosultam-annulated thiopyranoindole derivatives is reported which proceeds via domino Knoevenagel / intramolecular hetero-Diels–Alder reactions of ( E )- N -alkyl-2-aryl- N -(2-formylphenyl)ethene-1-sulfonamides with indoline-2-thiones in water. The products were obtained regioselectively in high yields.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02672-x