SYNTHESIS OF 2,3-DIHYDRO-1H,4H,6H-FURO{[}3,4-B]PYRROLO{[}1,2-A]QUINOLINE-6A(7H)-CARBO NITRILE - A NOVEL TYPE OF INTRAMOLECULAR TETRAHYDROFURAN FORMATION / VERBOOM W,MORZHERIN Y,KELDERMAN E,ENGBERSEN JFJ,VANHUMMEL GJ,HARKEMA S,REINHOUDT DN // RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY. - 1993. - V. 112, l. 10. - P. 549-551.

ISSN/EISSN:

0165-0513 / нет данных

Type:

Article

Abstract:

Approximately 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)-carbo nitrile (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.

Author keywords:

RING-CLOSURE REACTIONS; HETEROCYCLIC SYNTHESIS; STEREOCHEMICAL ASPECTS; AMINO; PYRROLO<1,2-A>QUINOLINES

DOI:

нет данных

Web of Science ID:

ISI:A1993MJ41800005

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	OCT
Publisher	ELSEVIER SCIENCE BV
Address	PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS
Language	English
Keywords-Plus	RING-CLOSURE REACTIONS; HETEROCYCLIC SYNTHESIS; STEREOCHEMICAL ASPECTS; AMINO; PYRROLO<1,2-A>QUINOLINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
ResearcherID-Numbers	Harkema, Sybolt/E-9526-2011 Reinhoudt, David/K-4767-2012 Morzherin, Yury/M-7420-2013
ORCID-Numbers	Morzherin, Yury/0000-0002-1333-6676
Number-of-Cited-References	14
Usage-Count-Since-2013	2
Journal-ISO	Recl. Trav. Chim. Pays-Bas-J. Roy. Neth. Chem. Soc.
Doc-Delivery-Number	MJ418