A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin

Mervat S.Sammor; Mustafa M.El-Abadelah; Ahmad Q.Hussein; Firas F.Awwadi; Salim S.Sabri; WolfgangVoelter

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A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin

机译：3-烷基（芳基）咪唑与茚三酮酰基吡啶的反应研究

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The reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines (1) with ninhydrin in dichloromethane at room temperature delivered good yields of the respective 2-hydroxy-2-(imidazo[1,5-a]pyridine-1-yl)indene-1,3-diones. In the presence of dimethyl acetylenedicarboxylate (DMAD), this uncatalyzed electrophilic substitution reaction, involving C-1 (in 1) and the central C=O (in ninhydrin), takes precedence over the three-component 1,4-dipolar cycloaddition reaction. This selectivity is probably due to the higher electrophilicity of the carbonyl carbon-2 in ninhydrin as compared to that of the sp-carbon atoms in DMAD, augmented with the high nucleophilicity of carbon-1 in 1.

机译：3-烷基（芳基）咪唑[1,5-a]吡啶（1）与茚三酮在室温下的二羟基丙氨酸的反应输送了相应的2-羟基-2-（咪唑[1,5-a]吡啶的良好产率 -1-yl）茚 - 1,3-致力。在乙酰二羧酸二甲甲酸二甲酯（DMAD）的存在下，该未催化的亲析电子替代反应涉及C-1（1）和中央C = O（在茚三酮中），优先于三组分1,4-偶极环加油反应。与DMAD中的SP-碳原子相比，这种选择性可能是由于茚三酮中的羰基碳-2的电泳较高，而碳-1中的高亲核性。

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来源
《Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences》 |2018年第6期|共9页
作者
Mervat S.Sammor; Mustafa M.El-Abadelah; Ahmad Q.Hussein; Firas F.Awwadi; Salim S.Sabri; WolfgangVoelter;
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Department of Chemistry Faculty of Science The University of Jordan Amman 11942 Jordan;

Department of Chemistry Faculty of Science The University of Jordan Amman 11942 Jordan;

Department of Chemistry Faculty of Science The University of Jordan Amman 11942 Jordan;

Department of Chemistry Faculty of Science The University of Jordan Amman 11942 Jordan;

Department of Chemistry Faculty of Science The University of Jordan Amman 11942 Jordan;

Interfakult?res Institut für Biochemie Universit?t Tübingen Hoppe-Seyler Stra?e 4 72076 Tübingen Germany;

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原文格式 PDF
正文语种 eng
中图分类化学;
关键词
2-hydroxy-2-(imidazo1; 5-apyridinyl)indenediones; electrophilic substitution; imidazo1; 5-apyridines; ninhydrin; X-ray structure;

机译：2-羟基-2-（Imidazo [1;1;5-A]吡啶基）否定硫化物;亲电子取代;咪唑唑[1;5-A]吡啶;茚三酮;X射线结构;

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专利

1. A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin [J] . Mervat S.Sammor, Mustafa M.El-Abadelah, Ahmad Q.Hussein, Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences . 2018,第6期

机译：3-烷基（芳基）咪唑与茚三酮酰基吡啶的反应研究
2. Microwave-prompted rapid and efficient synthesis of 3-alkyl substituted imidazo1,5-a pyridines [J] . Lai Bao Wang, Jia Pan, Can Ling Tang, 中国化学快报（英文版） . 2007,第004期

机译：微波促进的3-烷基取代的咪唑并1,5-a吡啶的快速有效合成
3. Complexes with 3-(pyridin-2-yl)imidazo[1,5-a]pyridine ligands by spontaneous dimerization of pyridine-2-carboxaldehyde within the coordination sphere of manganese(ii) in a one-pot reaction [J] . álvarez C.M., álvarez-Miguel L., García-Rodríguez R., Dalton transactions: An international journal of inorganic chemistry . 2012,第23期

机译：通过一锅反应在锰（ii）的配位范围内吡啶-2-甲醛的自发二聚反应，与3-（吡啶-2-基）咪唑并[1,5-a]吡啶配体形成配合物
4. Abnormal nucleophilic reaction of the α-carbon of α,β-unsaturated ester: A Easy Way to Form a Novel Imidazo1,5-a pyridine derivatives [C] . Hongmei Li International symposium for Chinese organic chemists . 2000

机译：α，β-不饱和酯的α-碳的异常亲核反应：形成新型咪唑的简单方法1,5-a吡啶衍生物
5. Synthesis and application of imidazo[1,5-a]pyridinium ions. [D] . Hutt, Johnathon Thomas. 2013

机译：咪唑并[1,5-a]吡啶鎓离子的合成和应用。
6. A comparative study of the cardiovascular and biochemical actions of the imidazo 45b pyridine sulmazole and an imidazo 45c pyridine analogue BW A746C. [O] . G. Allan, D. Cambridge, M. J. Follenfant, 1988

机译：咪唑并45b吡啶磺胺唑和咪唑并45c吡啶类似物BW A746C对心血管和生化作用的比较研究。
7. Reactions of 8-(Triphenylphosphoimino)quinoline with Aryl Aldehydes and Aryl Isocyanates : Formation of 2-Aryl-4H-imidazo[4,5,1-ij]quinolines and Related Systems [O] . Nagamatsu, Kentaro, Akiyoshi, Erina, Ito, Hidenori, 2006

机译：8-（Triphenylphosphoimino）quinoline与芳醛和芳基异氰酸酯的反应：2-Aryl-4H-咪唑并[4,5,1-ij]喹啉的形成及相关体系

A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin

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