Publication: Synthesis of 4-(Phenylamino)quinazoline-2(1H)-selones and Diselenides from Isoselenocyanates: Dimroth Rearrangement of an Intermediate
Synthesis of 4-(Phenylamino)quinazoline-2(1H)-selones and Diselenides from Isoselenocyanates: Dimroth Rearrangement of an Intermediate
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Atanassov, P. K., Linden, A., & Heimgartner, H. (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. https://doi.org/10.1002/hlca.200490166
Abstract
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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. U
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- Atanassov, Plamen K
- Heimgartner, Heinz
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Atanassov, P. K., Linden, A., & Heimgartner, H. (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. https://doi.org/10.1002/hlca.200490166
