Dimethylamino-substituted 7H-Benzo[de]pyrazolo[5,1-a]isoquinolin-7-ones and Their Behavior under Vilsmeier-Haack Conditions |
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Authors: | O N Lyubenko I G Ermolenko L D Patsenker Krasovitskii I N Tur |
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Institution: | (1) Ukraine National Academy of Sciences, Institute of Monocrystals, Kharkov, 61001, Ukraine |
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Abstract: | The behavior of dimethylamino-substituted 7H-benzode]pyrazolo5,1-a]isoquinoline-7-ones, synthesized for the first time, under conditions of the Vilsmeier-Haack reaction. It has been shown that, on heating with POCl3 and DMF, they are converted by electrophilic substitution at the position ortho to the dimethylamino group, followed by cyclization of the iminium adduct to a quinazolinium salt. When an acetyl group is present, the Arnold reaction, leading to the formation of a chloroaryl, accompanies the heterocyclization. The rates and proportion of the reaction products depend on the position of the dimethyl groups relative to the pyrazole ring. |
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Keywords: | 7H-benzo[de]pyrazolo[5 1-a]isoquinoline-7-ones quinazolinium salts heterocyclization heterocyclization the Vilsmeier-Haack reaction |
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