Mn(III)-Based Oxidation of (Methylene)Bis(Cyclodiamide)s. Facile Synthesis of Tetraazadispiro-(Undecanone)s and -(Tridecanone)s

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC

Journal of Heterocyclic Chemistry Pub Date : 2024-09-15 DOI:10.1002/jhet.4891

Haruki Kamachi, Takumi Toki, Ayaka Nakamura, Hiroshi Nishino

引用次数: 0

Abstract

The oxidation of 5,5′-(methylene)bis(6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione) monopiperidinium salts with Mn(OAc)₃•2H₂O was carried out in boiling MeCN, producing 2,4,9,11-tetramethyl-2,4,9,11-tetraazadispiro[5.0.5⁷.1⁶]tridecane-1,3,5,8,10,12-hexaones in high yields. A similar reaction using 4,4′-(methylene)bis(1,2-diphenylpyrazolidine-3,5-dione)s gave 2,3,8,9-tetraphenyl-2,3,8,9-tetraazadispiro[4.0.4⁶.1⁵]undecane-1,4,7,10-tetraones in good yields. The structure determination and the reaction mechanism for the formation of the unique tetraazadispiro(cyclopropane)s are discussed.

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基于锰(III)的(亚甲基)双(环二胺)氧化。四氮双螺-(十一烷酮)和-(十三烷酮)的简单合成

在沸腾的 MeCN 中用 Mn(OAc)3-2H2O 对 5,5′-(亚甲基)双(6-羟基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮)单哌啶盐进行氧化，生成 2,4,9,11-四甲基-2,4,9,11-四氮杂双螺[5.0.57.16]tridecane-1,3,5,8,10,12-hexaones 的高产率。使用 4,4′-（亚甲基）双(1,2-二苯基吡唑烷-3,5-二酮)s 进行类似反应，可以得到 2,3,8,9-四苯基-2,3,8,9-四氮杂二螺[4.0.46.15]十一烷-1,4,7,10-四酮，收率很高。本文讨论了独特的四氮杂双螺（环丙烷）的结构确定和生成反应机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.