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

Mostafa Kiamehr; Fahimeh Khademi; Behzad Jafari; Peter Langer

doi:10.1007/5419

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

Mostafa Kiamehr, Fahimeh Khademi, Behzad Jafari, Peter Langer

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.

Keywords

benzosultams; thiopyranoindole; cyclizations; domino reactions; regioselectivity.

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Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv

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