EFFICIENT SYNTHESIS OF PENTACYCLIC BENZOSULTAM-ANNULATED THIOPYRANOINDOLES <i>VIA</i> DOMINO KNOEVENAGEL / INTRAMOLECULAR HETERO-DIELS–ALDER REACTIONS IN WATER

Authors

  • Mostafa Kiamehr
  • Fahimeh Khademi
  • Behzad Jafari
  • Peter Langer Institut für Chemie, Abteilung für Organische Chemie, Albert-Einstein-Straße 3a, 18059 Rostock, Germany

DOI:

https://doi.org/10.1007/5419

Keywords:

benzosultams, thiopyranoindole, cyclizations, domino reactions, regioselectivity.

Abstract

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.

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Published

2020-04-01

Issue

Vol. 56 No. 3 (2020)

Section

Original Papers