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Synthesis of 4-(Phenylamino)quinazoline-2(1H)-selones and Diselenides from Isoselenocyanates: Dimroth Rearrangement of an Intermediate


Atanassov, Plamen K; Linden, Anthony; Heimgartner, Heinz (2004). Synthesis of 4-(Phenylamino)quinazoline-2(1H)-selones and Diselenides from Isoselenocyanates: Dimroth Rearrangement of an Intermediate. Helvetica Chimica Acta, 87(7):1873-1887.

Abstract

The reaction of anthranilonitriles 8 with phenyl isoselenocyanates (1a) in dry pyridine under reflux gave 4-(phenylamino)quinazoline-2(1H)-selones 9 (Scheme 2). They are easily oxidized and converted to diselenides of type 11. The analogous reaction of 8a with phenyl isothiocyanate (1b) yielded the quinazoline-2(1H)-thione 10 (Scheme 2). A reaction mechanism via a Dimroth rearrangement of the primarily formed intermediate is presented in Scheme 3. The molecular structures of 10 and 11a have been established by X-ray crystallography. Unexpectedly, no selone or diselenide was obtained in the case of the reaction with 3-aminobenzo[b]furan-2-carbonitrile (14). The only product isolated was the selenide 16 (Scheme 4), the structure of which has been established by X-ray crystallography.

Abstract

The reaction of anthranilonitriles 8 with phenyl isoselenocyanates (1a) in dry pyridine under reflux gave 4-(phenylamino)quinazoline-2(1H)-selones 9 (Scheme 2). They are easily oxidized and converted to diselenides of type 11. The analogous reaction of 8a with phenyl isothiocyanate (1b) yielded the quinazoline-2(1H)-thione 10 (Scheme 2). A reaction mechanism via a Dimroth rearrangement of the primarily formed intermediate is presented in Scheme 3. The molecular structures of 10 and 11a have been established by X-ray crystallography. Unexpectedly, no selone or diselenide was obtained in the case of the reaction with 3-aminobenzo[b]furan-2-carbonitrile (14). The only product isolated was the selenide 16 (Scheme 4), the structure of which has been established by X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2004
Deposited On:19 Aug 2013 06:14
Last Modified:05 Apr 2016 16:55
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200490166

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