Abstract
2-(3,3-Dimethyl-3,4-dihydro-2H-isoquinolin-1-ylidene)acetonitrile containing an enamine fragment has been acylated using acetyl or benzoyl chlorides to give the corresponding enamino ketones. The acylation using oxalyl chloride gives 5,5-dimethyl-2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]-isoquinoline-1-carbonitrile. Reaction of the latter with guanidine carbonate or o-phenylenediamine is accompanied by opening of the pyrrole ring and heterocyclization to give the corresponding 2-amino-4-imidazolone and 2-quinoxalone derivatives. Linear amines were formed in similar reactions with m-toluidine, 1-aminoadamantane, o-aminophenol, and 2-amino-3-hydroxypyridine.
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