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Cyclizations of N-alkyl-substituted azinium cations with bifunctional nucleophiles. 28. Orientation of the nucleophile in the reaction of quinoxalinium salts with indan-1,3-dione

✍ Scribed by G. M. Petrova; M. G. Ponizovskii; V. N. Charushin; G. G. Aleksandrov; E. O. Sidorov; O. N. Chupakhin

Book ID: 104785721
Publisher: Springer US
Year: 1990
Tongue: English
Weight: 617 KB
Volume: 26
Category: Article
ISSN: 0009-3122
DOI: 10.1007/bf00487435

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✦ Synopsis

In reactions with quinoxalinium salts in alcoholic-base media indan-l,3-dione acts as a C nucleophile, adding at the 2 or 3 position of the heterocycle to give the corresponding ylidene derivatives; attack by the nucleophile at the C(a) atom (the # position relative to the quaternary nitrogen atom) is preceded by addition of alcohol at the # position. Dissociative substitution at the C(2) atom in 2-alkoxy-3-(1,3-dioxoindan-2ylidene)-1,2,3,4-tetrahydroquinoxalines by another nucleophile makes it possible to regard lyate complexes as probable intermediates in cyclizations of l,4-diazinium salts with dinucleophiles.

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