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

✍ Scribed by Plamen K. Atanassov; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
432 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The reaction of anthranilonitriles 8 with phenyl isoselenocyanates (1a) in dry pyridine under reflux gave 4‐(phenylamino)quinazoline‐2(1__H__)‐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(1__H__)‐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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