Synthesis of 2-(4-quinazolinyl)ethyl sulfides via addition of thiols to 4-vinylquinazolines

Reaction of vinyl and isopropenyl Grignard reagents with quinazoline results in addition to the 3,4‐imine bond to give the 4‐alkenyldihydroquinazolines 4 which are conveniently aromatized with potassium ferri‐cyanide to the 4‐alkenylquinazolines 5. Quinazolines 5 undergo addition with thiols under n...

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Veröffentlicht in:Journal of heterocyclic chemistry 1997-07, Vol.34 (4), p.1263-1266
Hauptverfasser: Samaritoni, Jack G., Babbitt, George E.
Format: Artikel
Sprache:eng
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Zusammenfassung:Reaction of vinyl and isopropenyl Grignard reagents with quinazoline results in addition to the 3,4‐imine bond to give the 4‐alkenyldihydroquinazolines 4 which are conveniently aromatized with potassium ferri‐cyanide to the 4‐alkenylquinazolines 5. Quinazolines 5 undergo addition with thiols under neutral conditions to afford the quinazolinylethyl sulfides 2 in moderate yields.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570340429