Studies on Seven-membered Ring Compounds. XVIII. Reactions of the Quaternary Ammonium Salts of Cycloheptimidazole Derivatives

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概要

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• The quaternary ammonium salt 1-alkylcycloheptimidazol-2(1H)-one afforded1-alkylamino-7-alkyliminocycloheptatriene on heating with alkali. However, treatment of this salt with dilute aqueous sodium hydroxide at room temperature gave a ditropyl ether derivative. Action of active methylene compounds on the ammonium salt in the presence of sodium ethoxide yielded 6-substituted derivatives, which were easily dehydrogenated to the corresponding heptafulvene derivatives. As an example, the reaction of 2-oxo-1,3-dibenzyl-1,2-dihydrocycloheptimidazolinium chloride with ethyl cyanoacetate afforded 6-[cyano(ethoxycarbonyl)methyl]-1,3-dibenzyl-3,6-dihydrocycloheptimidazol-2(1H)-one, which was dehydrogenated to 6-[cyano(ethoxycarbonyl)methylene]-1,3-dibenzyl-3,6-dihydrocycloheptimidazol-2(1H)-one on heating with ethanol. This reaction made it clear that the quaternary ammonium salt has tropylium ion structure. Such reaction occurred also I case of 2-phenylcycloheptimidazole methiodide. The quaternary ammonium salts of 2-amino-and 2-methylthiocycloheptimidazole afforded 1-alkylcycloheptimidazol-2(1H)-one on treatment with acid.

• 公益社団法人日本薬学会の論文
• 1965-07-25

著者

• 中尾 英雄

  Research Laboratories, Sankyo Co., Ltd.

• 中尾 英雄

  Sankyo Research Laboratories, Sankyo Co., Ltd.,

• 中尾 英雄

  Sankyo Research Laboratories Sankyo Co. Ltd.

関連論文

• Studies on Seven-membered Ring Compounds. XX. Reactions of Troponeimine Derivatives. (2)
• Studies on Seven-membered Ring Compounds. XVII. Alkylation of Cycloheptimidazolone and Cyclohepta[b]pyrrolone
• Studies on Seven-membered Ring Compounds. XVI. Synthesis of 2-Substituted Cycloheptimidazole Derivatives
• Studies on Seven-membered Ring Compounds. XIV. Reactions of 2-Methoxytropone and 2-Halotropone with Hydrazides
• Studies on Seven-membered Ring Compounds. XIII. Reaction of 2-Bromo-7-methoxytropone with Active Methylene Compounds
• Studies on Orally Active Cephalosporin Esters. II. : Chemical Stability of Pivaloyloxymethyl Esters in Phosphate Buffer Solution
• Studies on Orally Active Cephalosporin Esters. III. : Effect of the 3-Substituent on the Chemical Stability of Pivaloyloxymethyl Esters in Phosphate Buffer Solution
• Studies on Seven-membered Ring Compounds. XVIII. Reactions of the Quaternary Ammonium Salts of Cycloheptimidazole Derivatives

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