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翻訳と辞書　辞書検索 [ 開発暫定版 ] スポンサード リンク Petrenko-Kritschenko piperidone synthesis ： ウィキペディア英語版 Petrenko-Kritschenko piperidone synthesis The Petrenko-Kritschenko reaction is a classic multicomponent-name reaction〔Jie-Jack Li; "Name reactions in heterocyclic chemistry"; 2005 John Wiley & Sons; ISBN 0-471-30215-5; pp313〕 that is closely related to the Robinson–Schöpf tropinone synthesis, but was published 12 years earlier. ==Classic reaction== In the original publication〔P. Petrenko-Kritschenko "Über die Kondensation des Acetondicarbonsäureesters mit Aldehyden, Ammoniak und Aminen" Journal für Praktische Chemie Volume 85, Issue 1, pages 1–37, 20 May 1912; 〕 diethyl-α-ketoglurate, a derivative of acetonedicarboxylic acid, is used in combination with ammonia and benzaldehyde. The relative stereochemistry was not elucidated in the original publication, structural analysis using X-rays or NMR was not available in these days. In the absence of ammonia or ammonium salts a 4-oxotetrahydropyran is formed.〔P. Petrenko-Kritschenko "Über Tetrahydropyronverbindungen" Journal für Praktische Chemie; Volume 60, Issue 1, pages 140–158, 27 December 1899; 〕 In contrast to the Robinson synthesis, it does not employ dialdehydes like succinaldehyde or glutaraldehyde but simpler aldehydes like benzaldehyde. Therefore the product of the reaction is not a bicyclic structure (see tropinone and pseudopelletierine) but a 4-piperidone. The synthesis of tropinone can be seen as a variation of the Petrenko-Kritschenko reaction in which the two aldehyde functions are covalently linked in a single molecule. Apart from the Hantzsch synthesis the Petrenko-Kritschenko reaction is one of the few examples in which a symmetric pyridine precursor can be obtained in a multicomponent ring-condensation reaction followed by an oxidation. The oxidation by chromium trioxide in acetic acid leads to a symmetrically substituted 4-pyridone, decarboxylation yields the 3,5-unsubstituted derivative.〔 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Petrenko-Kritschenko piperidone synthesis」の詳細全文を読む スポンサード リンク 翻訳と辞書 : 翻訳のためのインターネットリソース Copyright(C) kotoba.ne.jp 1997-2016. All Rights Reserved.