α，β-不饱和烯醛或烯酮二甲基腙的改进合成

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-12-06 DOI:10.1007/s11172-024-4427-z

A. B. Koldobskii, A. A. Druzina, O. S. Shilova

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引用次数: 0

摘要

用碘化甲基处理的β-二甲胺甲基取代羰基化合物的二甲基腙在三烷基胺基上发生化学选择性甲基化。随后用碱处理所得碘甲基化产物，高产出α、β-不饱和烯醛或烯酮的二甲基腙。对碱稳定的不饱和腙，最佳裂解剂为KOH水溶液；如果底物中存在不稳定的三甲基硅基，则1,8-重氮杂环[5.4.0]十一-7-烯（DBU）的效果最好。

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An improved synthesis of α,β-unsaturated enal or enone dimethylhydrazones

Dimethylhydrazones of β-dimethylaminomethyl-substituted carbonyl compounds treated with methyl iodide underwent chemoselective methylation at the trialkylamino group. Subsequent treatment of the resulting iodomethylates with bases yielded dimethylhydrazones of α,β-unsaturated enals or enones in high yields. For unsaturated hydrazones, which were stable to bases, the optimal cleaving agent was an aqueous solution of KOH; if labile trimethylsilyl groups were present in the substrate, the best results were obtained with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.