Synthesis of substituted 3-amino-4-cyano-1-oxo-1,2,5,10-tetrahydroazepino [3,4-b]indoles |
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Authors: | Reinhard Troschütz Annin Hoffmann |
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Abstract: | The preparation of 3-amino- and 3-dialkylamino-4-cyanoazepino3,4-fc]indoles bearing substituents on the aromatic nucleus and N10 is outlined. Starting from suitable substituted ethyl 3-formylindole-2-carboxy-latcs 2 , condensation with malononitrile ( 3 ) and subsequent sodium borohydride-reduction yielded ethyl 3-(2,2-dicyanoethyl)indole-2-carboxylates 5 and 19 , respectively, which were cyclized in boiling alkoxides to 3-alkoxy-4-cyanoazepino3,4-b]indoles 10,11,20 and 21 . This sequence constitutes a novel and flexible route to functional azepino3,4-b>]indoles. The aminolysis of 10,11,20 and 21 with different amines and ammonia yielded the title compounds which were screened for their possible biological activity. |
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