Volume 21, Issue 22
Heterocyclic Compounds
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ChemInform Abstract: Formation of a Benzopyrylium Ion and a Quinoline from Benzofuran.

H. SONNENSCHEIN

H. SONNENSCHEIN

Cent. Inst. Org. Chem., Acad. Sci. DDR, DDR-1199 Berlin

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E. SCHMITZ

E. SCHMITZ

Cent. Inst. Org. Chem., Acad. Sci. DDR, DDR-1199 Berlin

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W. PRITZKOW

W. PRITZKOW

Cent. Inst. Org. Chem., Acad. Sci. DDR, DDR-1199 Berlin

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First published: May 29, 1990

Abstract

Phenylchlorocarbene, generated from the phenylchloroazirine (II), reacts with benzofuran (I) to give the cyclopropane derivative (III).

ChemInform Abstract

Phenylchlorocarbene, generated from the phenylchloroazirine (II), reacts with benzofuran (I) to give the cyclopropane derivative (III). On heating, this compound undergoes cleavage of the cyclopropane moiety to afford the benzopyrylium chloride (IV), an unstable intermediate which reacts with aniline (V) to yield the quinoline (VI).

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