Synthesis of 2-amino-8-benzylidene-4-phenyl-3,4,5,6,7,8-hexahydro- and -5,6,7,8-tetrahydroquinazoline derivatives

Author:

Deli József,Lóránd Tamás,Szabó Dezsö,Földesi András,Zschunke Adolf

Abstract

Base-catalyzed reaction of 2,6-dibenzylidenecyclohexanone and alkylguanidines gave 2-alkylamino-8-benzylidene-4-phenyl-3,4,5,6,7,8-hexahydroquinazolines IVa-c, which were oxidized to 2-alkylamino-8-benzylidene-4-phenyl-5,6,7,8-tetrahydroquinazolines Va-c. The acylamino (VIa-c, VIIa-d, IXa,b) and diacylamino derivatives (VIIIa,b) of the 2-amino-8-benzylidene-4-pheny]-3,4,5,6,7,8-hexahydroquinazoline (II), 2-amino-8-benzylidene-4-phenyl-5,6,7,8-tetrahydroquinazoline (III) and compounds Va-c have also been prepared. These compounds having the E-configuration were converted into the Z isomers XIIa-e by photoisomerization. The structures were confirmed by spectroscopic methods (IR, 1H NMR, 13C NMR).

Publisher

Institute of Organic Chemistry & Biochemistry

Subject

General Chemistry

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