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  1. 学術雑誌論文

Mechanistic aspect of ring transformations in the reaction of 5-nitro-4-pyrimidinone with acetophenone derivatives and cycloalkanones depending on the electron density/ring size of the ketone

http://hdl.handle.net/10173/1349
http://hdl.handle.net/10173/1349
605ad35b-1699-4c05-af99-cf05a286728a
名前 / ファイル ライセンス アクション
27-23.pdf 27-23.pdf (135.8 kB)
Item type 学術雑誌論文 / Journal Article(1)
公開日 2016-03-25
タイトル
タイトル Mechanistic aspect of ring transformations in the reaction of 5-nitro-4-pyrimidinone with acetophenone derivatives and cycloalkanones depending on the electron density/ring size of the ketone
言語
言語 eng
資源タイプ
資源タイプ識別子 http://purl.org/coar/resource_type/c_6501
資源タイプ journal article
著者 Nishiwaki, Nagatoshi

× Nishiwaki, Nagatoshi

Nishiwaki, Nagatoshi

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Sugimoto, Ryuichi

× Sugimoto, Ryuichi

Sugimoto, Ryuichi

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Saigo, Kazuhiko

× Saigo, Kazuhiko

Saigo, Kazuhiko

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Kobiro, Kazuya

× Kobiro, Kazuya

Kobiro, Kazuya

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内容記述タイプ Abstract
内容記述 3-Methyl-5-nitro-4-pyrimidinone undergoes two kinds of nucleophilic type ring transformations upon treatment with cycloalkanones in the presence of ammonium acetate, which affords 4,5-disubstituted pyrimidines and 5,6-disubstituted 3-nitro-2-pyridones. In order to improve the synthetic utility of this reaction, it is necessary to control the regioselectivity of these ring transformations. In the present work, we performed DFT calculation to realize the selectivity of two ring transformation products. In cases of adduct intermediates derived from cyclohexanone and cyclooctanone, the 2-attack proceeds preferably to give condensed pyrimidines. On the other hand, the adduct intermediate derived from cycloheptanone undergoes the 4-attack predominantly to afford condensed nitropyridone.
書誌情報 Tetrahedron Letters

巻 54, 号 8, p. 956-959, 発行日 2013
DOI
関連タイプ isVersionOf
識別子タイプ DOI
関連識別子 10.1016/j.tetlet.2012.12.020
著者版フラグ
出版タイプ AM
出版タイプResource http://purl.org/coar/version/c_ab4af688f83e57aa
出版者
出版者 Elsevier Ltd.
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