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在微波辐射下高效合成吡哆醛肟衍生物。

An efficient synthesis of pyridoxal oxime derivatives under microwave irradiation.

机构信息

Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Kuhačeva 20, 31000 Osijek, Croatia.

University of Zagreb, Faculty of Textile Technology, Department of Applied Chemistry, Prilaz baruna Filipovića 28a, 10000 Zagreb, Croatia.

出版信息

Molecules. 2014 Jun 6;19(6):7610-20. doi: 10.3390/molecules19067610.

DOI:10.3390/molecules19067610
PMID:24914903
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271574/
Abstract

Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%-94%) were obtained in acetone in very short reaction times (3-5 min) as well as in the solvent-free procedure (42%-78%) in very short reaction times (7-10 min) too. Effective metodologies for the preparation of pyridoxal oxime quaternary salts, having the advantagies of being eco-friendly, easy to handle, and performed in shorter reactions time are presented. The structure of compound 7, in which a 4-fluorophenacyl moiety is bonded to the pyridinium ring nitrogen atom, was unequivocally confirmed by the single-crystal X-ray diffraction method.

摘要

已通过用取代的苯乙酮溴化物季铵化吡哆醛肟,合成了吡哆醛肟的季铵盐。微波加热下,在溶剂(丙酮)中和无溶剂条件下都可以进行微波辅助快速合成。在短时间(3-5 分钟)内,在丙酮中以及在无溶剂条件下(7-10 分钟)都可以获得良好到优秀的收率(58%-94%)。本文介绍了一种有效制备吡哆醛肟季铵盐的方法,该方法具有环保、易于操作和短反应时间的优点。通过单晶 X 射线衍射方法明确确认了化合物 7 的结构,其中 4-氟苯乙酮部分键合到吡啶鎓环氮原子上。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/688a/6271574/7cba1b58efef/molecules-19-07610-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/688a/6271574/e427de824902/molecules-19-07610-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/688a/6271574/32848595ea13/molecules-19-07610-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/688a/6271574/7cba1b58efef/molecules-19-07610-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/688a/6271574/e427de824902/molecules-19-07610-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/688a/6271574/32848595ea13/molecules-19-07610-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/688a/6271574/7cba1b58efef/molecules-19-07610-g002.jpg

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本文引用的文献

1
Synthesis and evaluation of novel analogues of vitamin B6 as reactivators of tabun and paraoxon inhibited acetylcholinesterase.新型维生素 B6 类似物的合成与评价及其对塔崩和对氧磷抑制乙酰胆碱酯酶的重活化作用。
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Structure validation in chemical crystallography.化学晶体学中的结构验证
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Oximes: Reactivators of phosphorylated acetylcholinesterase and antidotes in therapy against tabun poisoning.
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Current understanding of the application of pyridinium oximes as cholinesterase reactivators in treatment of organophosphate poisoning.目前对吡啶肟类化合物作为胆碱酯酶复活剂在有机磷中毒治疗中的应用的理解。
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