Synthesis of 2,3‐dihydro‐I H,4 H, 6 H‐furo[3,4‐b]pyrrolo[1,2‐a]quinoline‐6a(7H)‐carbonitrile; a novel type of intramolecular tetrahydrofuran formation

Willem Verboom, Yury Morzherin, Erik Kelderman, Johan F.J. Engbersen, David N. Reinhoudt, Gerrit J. van Hummel, Sybolt Harkema

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)

Abstract

Appropriately 4-substituted 1,2,3,3a,4,5-hexahydro-3a-(methoxymethyl)pyrrolo[1,2-a]quinolines 3 cyclize to 2,3-dihydro-1H,4H,6H-furo[3,4-b]pyrrolo[1,2-a]quinoline-6a(7H)-carbonitrile (5) upon heating in polar solvents, the reaction being accelerated by lithium bromide. The formation of the annulated tetrahydrofuran ring of 5 takes place via intramolecular attack of the oxygen atom of the methoxymethyl substituent at C-3a on the electrophilic carbon atom at C-4. The structure of 5 was confirmed by single-crystal X-ray structure determination.
Original languageEnglish
Pages (from-to)549-551
JournalRecueil des travaux chimiques des Pays-Bas
Volume112
Issue number10
DOIs
Publication statusPublished - 1993

Fingerprint Dive into the research topics of 'Synthesis of 2,3‐dihydro‐I H,4 H, 6 H‐furo[3,4‐b]pyrrolo[1,2‐a]quinoline‐6a(7H)‐carbonitrile; a novel type of intramolecular tetrahydrofuran formation'. Together they form a unique fingerprint.

  • Cite this