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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 3
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Original Articles

Reaction of Arylglyoxals with Electron‐Rich Benzenes and π‐Excessive Heterocycles. Facile Synthesis of Heteroaryl α‐Acyloins

Sergey P. Ivonin Department of Organic Chemistry, Dnepropetrovsk National University, Nauchnaya Street 13, Dnepropetrovsk, 49050, UkraineCorrespondence[email protected]
,
Andrey V. Lapandin Department of Organic Chemistry, Dnepropetrovsk National University, Nauchnaya Street 13, Dnepropetrovsk, 49050, Ukraine
,
Andrey A. Anishchenko Department of Organic Chemistry, Dnepropetrovsk National University, Nauchnaya Street 13, Dnepropetrovsk, 49050, Ukraine
&
Vasilii G. Shtamburg Department of Organic Chemistry, Dnepropetrovsk National University, Nauchnaya Street 13, Dnepropetrovsk, 49050, Ukraine
Pages 451-461 | Received 02 Jul 2003, Published online: 16 Aug 2006

Citations (22)

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Read on this site (2)

Sergey P. Ivonin, Andrey V. Lapandin & Anna V. Dolgikh. (2006) Reaction of Phenylglyoxal with Cyclopentenylmorpholine and its Arylidene Derivatives. Synthetic Communications 36:10, pages 1413-1417.
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Sergey P. Ivonin & Andrey V. Lapandin. (2004) Isomerization of Hetaryl Analogues of α‐Benzoins in Basic Media. Synthetic Communications 34:20, pages 3727-3735.
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Articles from other publishers (20)

Srinivasarao Yaragorla & Doma Arun. (2022) Arylation and Aryne Insertion into C-Acylimines: A Simple, Flexible, and Divergent Synthesis of C2-Aryl Indoles. The Journal of Organic Chemistry 87:21, pages 14250-14263.
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Jianguo Yang, Saimei Liu, Jing Gui, Daokai Xiong, Jinshan Li, Zhiming Wang & Jun Ren. (2022) HFIP-Promoted Selective Hydroxyalkylation of Aniline Derivatives with Arylglyoxal Hydrates. The Journal of Organic Chemistry 87:9, pages 6352-6361.
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Fernando Martínez‐Lara, Anisley Suárez, Noelia Velasco, Samuel Suárez‐Pantiga & Roberto Sanz. (2021) Gold‐Catalyzed Reactions of 2‐Alkynyl‐1‐indolyl‐1,2‐diols with Thiols: Stereoselective Synthesis of ( Z )‐α‐Indol‐3‐yl α‐(2‐Thioalkenyl) Ketones . Advanced Synthesis & Catalysis 364:1, pages 132-138.
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Atul Kumar, Javeed Rasool & Qazi Naveed Ahmed. 2022. Chemistry of 2-Oxoaldehydes and 2-Oxoacids. Chemistry of 2-Oxoaldehydes and 2-Oxoacids 63 171 .
Shahnawaz Khan, Atul Kumar, Raman Gupta & Qazi N. Ahmed. (2017) The Ritter Reaction of 2-Oxoaldehydes at Room Temperature: Divergent Behaviour towards Acid Strength.. ChemistrySelect 2:34, pages 11336-11340.
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Anisley Suárez, Fernando Martínez, Samuel Suárez-Pantiga & Roberto Sanz. (2017) PTSA-Catalyzed Reaction of Indoles with 2-Oxoaldehydes: Synthesis of α,α-Bis(indol-3-yl) Ketones. ChemistrySelect 2:2, pages 787-790.
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Cuiping Wang, Zhiqiang Zhang, Kui Liu, Jingbo Yan, Tiexin Zhang, Gonghao Lu, Qingtao Meng, Haijun Chi & Chunying Duan. (2017) Copper-catalyzed synthesis of indolyl diketones via C–H oxidation/diacylation of indoles with arylglyoxal hydrates. Organic & Biomolecular Chemistry 15:29, pages 6185-6193.
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Carlos Vila, Lucia Quintero, Gonzalo Blay, M. Carmen Muñoz & José R. Pedro. (2016) Organocatalytic Enantioselective Synthesis of α-Hydroxyketones through a Friedel–Crafts Reaction of Naphthols and Activated Phenols with Aryl- and Alkylglyoxal Hydrates. Organic Letters 18:21, pages 5652-5655.
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Guanghui Lü, Xu Cheng, Yang Zheng, Weijian Li, Li Hai & Yong Wu. (2016) Benzoic acid: an efficient and rapid catalyst for the synthesis of α-hydroxyl(indolyl)ethanones from indoles. Chemical Research in Chinese Universities 32:2, pages 212-218.
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Anisley Suárez, Fernando Martínez & Roberto Sanz. (2016) Synthesis of α-functionalized α-indol-3-yl carbonyls through direct S N reactions of indol-3-yl α-acyloins . Organic & Biomolecular Chemistry 14:47, pages 11212-11219.
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Yang Zheng, Ren-Jun Li, Zhen Zhan, Yan Zhou, Li Hai & Yong Wu. (2016) Fe-catalyzed regioselective Friedel–Crafts hydroxyalkylation of N -substituted glyoxylamide with indoles. Chinese Chemical Letters 27:1, pages 41-46.
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Nagaraju Mupparapu , Narsaiah Battini , Satyanarayana Battula , Shahnawaz Khan , Ram A. Vishwakarma  & Qazi Naveed Ahmed . (2014) Aminocatalytic Cross‐Coupling Approach via Iminium Ions to Different CC Bonds. Chemistry – A European Journal 21:7, pages 2954-2960.
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Mohammad Anary-Abbasinejad & Mahdiyeh Talebizadeh. (2013) Reaction of arylglyoxals with pyrrole or indole in aqueous media: facile synthesis of heteroaryl α‐acyloins. Journal of the Iranian Chemical Society 11:4, pages 963-968.
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Bagher Eftekhari-Sis, Maryam Zirak & Ali Akbari. (2013) Arylglyoxals in Synthesis of Heterocyclic Compounds. Chemical Reviews 113:5, pages 2958-3043.
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Jakub Majer, Piotr Kwiatkowski & Janusz Jurczak. (2011) Enantioselective Friedel–Crafts Reaction of Acylpyrroles with Glyoxylates Catalyzed by BINOL–Ti(IV) Complexes. Organic Letters 13:22, pages 5944-5947.
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S. P. Ivonin, A. V. Mazepa & A. V. Lapandin. (2006) Mass-spectral behavior and thermal stability of hetaryl analogs of unsymmetrical benzoins. Chemistry of Heterocyclic Compounds 42:4, pages 451-457.
Crossref
S. P. Ivonin, A. V. Lapandin & V. G. Shtamburg. (2005) Interaction of N,N-dimethylhydrazonomethyl and α-hydroxyketone groups in hetaryl analogs of unsymmetrical benzoins. Chemistry of Heterocyclic Compounds 41:12, pages 1484-1493.
Crossref
S. P. Ivonin & A. V. Lapandin. (2005) Interaction of 3-Substituted Indoles with Phenylglyoxal. Chemistry of Heterocyclic Compounds 41:11, pages 1390-1393.
Crossref
Sergey�P. Ivonin, Andrey�V. Lapandin, Andrey�A. Anishchenko & Vasilii�G. Shtamburg. (2004) Mutual Influence of (Dimethylhydrazono)methyl Groups and ?-Hydroxy Ketone Moieties in Hetaryl Analogues of Unsymmetric Benzoins. European Journal of Organic Chemistry 2004:22, pages 4688-4693.
Crossref
Sergey P. Ivonin, Andrey V. Lapandin, Andrey A. Anishchenko & Vasilii G. Shtamburg. (2004) Reaction of Arylglyoxals with Electron‐Rich Benzenes and π‐Excessive Heterocycles. Facile Synthesis of Heteroaryl α‐Acyloins.. ChemInform 35:29.
Crossref

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