Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Electrophilic Substitution Reactions of 2-Aminotropone and Its N-Alkyl Derivatives
Tetsuo NozoeShoji RyuTakashi Toda
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1968 Volume 41 Issue 12 Pages 2978-2984

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Abstract

The electrophilic substitution reactions of 2-aminotropone (I), 2-methylaminotropone (II), and 2-dimethylaminotropone (III) were investigated. The structure of the products was proved by hydrolysis to lead to known tropolone derivatives. By the nitrosation of II, N-nitroso-2-methylaminotropone was obtained in a good yield; this compound is a new type of active troponoid compound. The substitution reactions of III gave tropolone derivatives, accompanied by the hydrolysis of the dimethylamino group. The mechanism of the hydrolysis is then discussed.

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