The Experts below are selected from a list of 282 Experts worldwide ranked by ideXlab platform
Jean-françois Paquin - One of the best experts on this subject based on the ideXlab platform.
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Use of XtalFluor-E as an Alternative to POCl3 in the Vilsmeier-Haack Formylation of C-2-Glycals.
The Journal of organic chemistry, 2018Co-Authors: Majdouline Roudias, Frederic Vallee, Julien Martel, Jean-françois PaquinAbstract:We report the use of XtalFluor-E ([Et2NSF2]BF4) as an alternative to POCl3 in the Vilsmeier-Haack Formylation reaction of C-2-glycals. Employing a XtalFluor-E/DMF combination allowed the desired C-2-formyl glycals to be isolated in 11-90% yield. This method was extended to the synthesis of a C-2 -formylated disaccharide glycal.
Mohammed Shafeeulla R - One of the best experts on this subject based on the ideXlab platform.
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Design, synthesis and characterization of new 1,2,3-triazolyl pyrazole derivatives as potential antimicrobial agents via a Vilsmeier–Haack reaction approach
RSC Advances, 2016Co-Authors: Manjunatha Bhat, Gundibasappa Karikannar Nagaraja, Reshma Kayarmar, S K Peethamber, Mohammed Shafeeulla RAbstract:The synthesis of a new series of 3-{5-methyl-1-[2-methyl-3-(trifluoromethyl) phenyl/substituted phenyl]-1H-1,2,3-triazol-4-yl}-1-(aryl)-1H-pyrazole-4-carbaldehyde compounds (5a–n) was carried out via a Vilsmeier–Haack Formylation of 4-{(1E)-1-[2-(aryl) hydrazinylidene]ethyl}-5-methyl-1-[2-methyl-3-(trifluoromethyl)phenyl/substituted phenyl]-1H-1,2,3-triazole (4a–n) with a phosphorous oxychloride and DMF mixture. The newly synthesized compounds were characterized using IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. The newly synthesized compounds were screened for their in vitro anti-bacterial, anti-fungal and anti-oxidant activities. Some of the synthesized compounds displayed a broad spectrum of antimicrobial activities and moderate to good anti-oxidant activities. The anti-bacterial results were further supported by in silico molecular docking studies of these compounds for the inhibition of E. coli MurB enzyme (PDB code: 2MBR) and showed a minimum binding energy and good affinity towards the active pocket comparable with the standard drug Ciproflaxin. Thus, they may be considered as good inhibitors of the E. coli MurB enzyme (PDB code: 2MBR).
Mikhail A. Kuznetsov - One of the best experts on this subject based on the ideXlab platform.
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Direct and Efficient Synthesis of Pyrrole‐3‐carbaldehydes by Vilsmeier—Haack Formylation of Pyrroles with Sterically Crowded Amides.
ChemInform, 2012Co-Authors: Petr V. Ilyin, Alena S. Pankova, Mikhail A. KuznetsovAbstract:The regioselectivity concerning the Formylation of various pyrroles with sterically crowded formamides is studied.
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Direct and Efficient Synthesis of Pyrrole-3-carbaldehydes by Vilsmeier–Haack Formylation of Pyrroles with Sterically Crowded Amides
Synthesis, 2012Co-Authors: Petr V. Ilyin, Alena S. Pankova, Mikhail A. KuznetsovAbstract:A simple and convenient synthetic method to prepare N-substituted pyrrole-3-carbaldehydes by Vilsmeier–Haack Formylation of pyrroles using sterically crowded formamides was developed. The dependence of the Formylation regioselectivity on steric features of substrates and reagents is discussed.
Yiwen Zhang - One of the best experts on this subject based on the ideXlab platform.
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Studies on the Total Synthesis of Some Biologically Active Natural Products: Neocosmosin A and the Discoipyrroles
2017Co-Authors: Yiwen ZhangAbstract:The body of this thesis is comprised of four scientific journal articles and a patent. It is preceded by an overview that contextualizes all of this submitted/published work. The first major part of this thesis is comprised of Publication 1. This is a review concerned with the chemical syntheses of the cochliomycins, including congener A, and certain related resorcylic acid lactones (RALs). pecifically, Publication 1 reviews the recently published literature on the cochliomycins and related, co-occurring RALs and is accompanied by a brief commentary on the source organisms and certain of their biological properties. It serves to contextualize some of the author’s other published research incorporated in the thesis. The second major part of this thesis is comprised of Publication 2. This details work concerned with establishing the true structure of the marine-derived RAL neocosmosin A. Specifically, the structure, A, originally assigned to neocosmosin A was synthesized with the key steps involving olefin-cross metathesis, ring-closing metathesis, palladium- catalyzed Meinwald rearrangement and Mitsunobu esterification reactions. A late-stage and simple modification to the reaction sequence also provided the enantiomer B that, in fact, represents the true structure of the natural product. The third major part of this thesis is comprised of Publication 3. This details the development of modular total syntheses of the marine-derived alkaloids discoipyrroles A and B. Specifically, the intermediates C and D (see below) were prepared from (parent) pyrrole using Ullmann-Goldberg and Suzuki-Miyaura cross-coupling, Vilsmeier-Haack Formylation, electrophilic bromination, and Wittig olefination reactions as key steps. A late stage MoOPH-mediated oxidative cyclization reaction was then employed to assemble the novel heterobicyclic core of the target discoipyrroles. The fourth major part of this thesis is comprised of Publication 4. This details the first total synthesis of the most structurally complex member of the small family of marine- derived discoipyrroles, namely congener D. This synthesis, which used methodology developed during the course of the aforementioned syntheses of the discoipyrroles A and B, involved, as key steps, the MoOPH-mediated oxidative cyclization of precursor E and this was followed by conjugate addition and redox processes. The fifth and final part of this thesis is comprised of Publication 5. This patent details inventions related to methods for preparing a variety of discoipyrrole-like compounds and novel analogues, as well as pharmaceutical compositions comprising these compounds and their possible use in therapeutic settings. For example, compound F, which incorporates a discoipyrrole-like core structure, was synthesized in four steps from indole and …
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Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway
Organic letters, 2016Co-Authors: Yiwen Zhang, Martin G. Banwell, Paul D. Carr, Anthony C. WillisAbstract:The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann–Goldberg and Suzuki–Miyaura cross-coupling, Vilsmeier–Haack Formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2).
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Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway
2016Co-Authors: Yiwen Zhang, Martin G. Banwell, Paul D. Carr, Anthony C. WillisAbstract:The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann–Goldberg and Suzuki–Miyaura cross-coupling, Vilsmeier–Haack Formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2)
Floris P. J. T. Rutjes - One of the best experts on this subject based on the ideXlab platform.
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Continuous flow production of thermally unstable intermediates in a microreactor with inline ir-analysis: Controlled Vilsmeier-Haack Formylation of electron-rich arenes
Organic Process Research & Development, 2012Co-Authors: S. A. M. W. Van Den Broek, J.r. Leliveld, René Becker, Marielle M. E. Delville, Pieter J. Nieuwland, Kaspar Koch, Floris P. J. T. RutjesAbstract:The Vilsmeier–Haack Formylation of aromatic compounds is a well-established process in organic synthesis, largely driven by the fact that the resulting aldehydes are generally useful intermediates for the synthesis of fine chemicals and pharmaceutical products. Industrial-scale production, however, is often hampered by laborious procedures requiring the use of hazardous chemicals to produce the highly reactive intermediates. In order to circumvent these issues, a flow chemistry approach was developed. This article describes the design and semiautomated optimization of the Vilsmeier–Haack Formylation in continuous flow and subsequent scale-up to preparative volumes in an intrinsically safe manner.
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Continuous Flow Production of Thermally Unstable Intermediates in a Microreactor with Inline IR-Analysis: Controlled Vilsmeier–Haack Formylation of Electron-Rich Arenes
2012Co-Authors: Sebastiaan (bas) A. M. W. Van Den Broek, J.r. Leliveld, Marielle M. E. Delville, Pieter J. Nieuwland, Kaspar Koch, René Becker, Floris P. J. T. RutjesAbstract:The Vilsmeier–Haack Formylation of aromatic compounds is a well-established process in organic synthesis, largely driven by the fact that the resulting aldehydes are generally useful intermediates for the synthesis of fine chemicals and pharmaceutical products. Industrial-scale production, however, is often hampered by laborious procedures requiring the use of hazardous chemicals to produce the highly reactive intermediates. In order to circumvent these issues, a flow chemistry approach was developed. This article describes the design and semiautomated optimization of the Vilsmeier–Haack Formylation in continuous flow and subsequent scale-up to preparative volumes in an intrinsically safe manner