ACYLATION REACTION OF THE 3,3-DIMETHYLISOQUINOLINE SERIES ENAMINONITRILE AND PROPERTIES OF 5,5-DIMETHYL-2,3-DIOXO-2,3,5,6-TETRAHYDROPYRROLO[2,1-<i>a</i>]ISOQUINOLINE-1-CARBONITRILE
DOI:
https://doi.org/10.1007/781Keywords:
1-aminoadamantane, 2-amino-3-hydroxypyridine, 2-amino-4-imidazolone, o-aminophenol, 5, 5-dimethyl-2, 3-dioxo-2, 3, 6-tetrahydropyrrolo[2, 1-a]isoquinoline-1-carbonitrile, 2-(3, 3-dimethyl-3, 4-dihydro-2H-isoquinolin-1-ylidene)acetonitrile, guanidine carbonate, o-phenylenediamine, 2-quinoxalone, m-toluidine, enamino ketones, linear amines, acylation, heterocyclizationAbstract
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.
Authors: A. G. Mikhailovskii, O. V. Surikova, P. A. Chugainov, and M. I. Vakhrin
English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (7), pp 974-979
