Reactions of 2-Formyl-3-methoxypropionitrile Derivatives as Electrophilic Reagent

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概要

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• The reaction of 2-formyl-3-methoxypropionitrile derivatives (I, II, III) with benzenes (VIa-h) in the presence of an acid catalyst gave cis isomers of 2-methoxymethylene-3-phenylpropionitriles (VIIa-h) via electrophilic substitution of allyl cation (IV). The aluminum chloride-catalyzed reaction of III with the benzenes afforded 2-methoxymethyl-3,3-diphenylpropionitriles (XVa-c) via electrophilic substitution of oxocarbonium ion (V). The same reactions of carbomethoxy analogs of I, II, and III were carried out to provide trans isomers of methyl 2-methoxymethylene-3-phenylpropionates (XIa-e) and a small amount of the carbomethoxy analog (XVIc) of XVc. In these reactions indan-(VIIIa, XIIa, b), triphenylpropane-(IXa, XIIIc), and indene-(XIVa, b) derivatives were obtainable via successive intra- or intermolecular substitutions of benzenes at the 2-methoxymethylene groups of VII and XI. The compounds VII and XV were converted into 2-dimethoxymethyl-3-phenylpropionitriles (X) and 2-cyano-1,1-diphenyl-1-propenes (XVII), respectively, by the treatment of sodium methoxide in methanol. Some heterocycles such as 3-cyano-2-methoxychroman (XIX), 3-cyano-2H-chromen (XXIII), and 3-cyanoquinoline (XXIV) were simply derived from I or III following the above methods.

• 社団法人日本薬学会の論文
• 1978-05-25

著者

• 安部 泰弘

  Production Department Shionogi And Co. Ltd.

• 田中 守

  Production Department Shionogi And Co. Ltd.

• 徳山 幹治

  Production Department, Shionogi and Co., Ltd.

• 徳山 幹治

  Production Department Shionogi And Co. Ltd.

関連論文

• Reactions of 2-Formyl-3-methoxypropionitrile Derivatives as Electrophilic Reagent
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• Decomposition of Dithiocarbamates. VII. The Decomposition of N-Monosubstituted Dithiocarbamic Acid in Alkaline Solutions
• Decomposition of Dithiocarbamates. VI. The Decomposition of N-Monosubstituted Dithiocarbamic Acids in Acidic Solutions
• Decomposition of Dithiocarbamates. V. The Dissociations of N-Monosubstituted Dithiocarbamic Acids in strongly Acidic and Alkaline Solutions
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• Polysaccharides in Lichens and Fungi. I. Antitumour Active Polysaccharides of Gyrophora esculenta MIYOSHI and Lasallia papulosa (ACH.) LANO

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