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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

✍ Scribed by Willem Verboom; Yury Morzherin; Erik Kelderman; Johan F. J. Engbersen; David N. Reinhoudt; Gerrit J. van Hummel; Sybolt Harkema

Book ID: 104589572
Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 310 KB
Volume: 112
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19931121006

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✦ Synopsis

Abstract

Appropriately 4‐substituted 1,2,3,3a,4,5‐hexahydro‐3a‐(methoxymethyl)pyrrolo[1,2‐a]quinolines 3 cyclize to 2,3‐dihydro‐1 H,4__H__,6__H__‐furo[3,4‐b]pyrrolo[1,2‐a]quinoline‐6a(7__H__)‐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.

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