The base-free van Leusen reaction of cyclic imines on water: synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives

2019 ◽  
Vol 17 (21) ◽  
pp. 5234-5238 ◽  
Author(s):  
Killari Satyam ◽  
V. Murugesh ◽  
Surisetti Suresh
Keyword(s):  
Van Leusen Reaction

Construction of imidazoles on dihydro β-carboline imines has been disclosed using the van Leusen reaction under base-free conditions on water.

scholarly journals Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis

2020 ◽  
Vol 13 (3) ◽  
pp. 37 ◽  
Author(s):  
Xunan Zheng ◽  
Zhengning Ma ◽  
Dawei Zhang
Keyword(s):  
Drug Discovery ◽  
Chemical Synthesis ◽  
Small Molecules ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
Structural Features ◽  
Pharmaceutical Companies ◽  
Recent Developments ◽  
Van Leusen Reaction

Imidazole and its derivatives are one of the most vital and universal heterocycles in medicinal chemistry. Owing to their special structural features, these compounds exhibit a widespread spectrum of significant pharmacological or biological activities, and are widely researched and applied by pharmaceutical companies for drug discovery. The van Leusen reaction based on tosylmethylisocyanides (TosMICs) is one of the most appropriate strategies to synthetize imidazole-based medicinal molecules, which has been increasingly developed on account of its advantages. In this review, we summarize the recent developments of the chemical synthesis and bioactivity of imidazole-containing medicinal small molecules, utilizing the van Leusen imidazole synthesis from 1977.

Synthesis of 1,3-Oxazoles via Van Leusen Reaction in a Pressure Reactor and Preliminary Studies of Cations Recognition

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 7
Author(s):  
Verónica G. García-Ramírez ◽  
Claudia Contreras-Celedón ◽  
Gabriela Rodriguez-García ◽  
Luis Chacón-García ◽  
Carlos J. Cortes-García
Keyword(s):  
Medicinal Chemistry ◽  
Reaction Times ◽  
Biological Relevance ◽  
Hybrid Molecules ◽  
Van Leusen Reaction

Six 1,3-oxazoles were synthetized in moderate to good yields by Van Leusen reaction in a pressure reactor. The methodology allowed to decrease the reaction times reported in the literature from hours to 20 min. In addition, preliminary qualitative recognition of cations with some synthetized oxazoles such as Hg2+, Ni2+, Zn2+, Ag+, Cu2+, Pb2+ was done and a “turn off” effect was observed with Ni2+. Finally, the 1,3-oxazoles could be of biological relevance because they are considered privileged nucleus in medicinal chemistry and therefore will be useful to obtain pharmacophoric hybrid molecules.

Tandem Copper-CatalyzedN-Arylation-Condensation and van Leusen Reaction: Synthesis of 1,4-Benzodiazepines and Imidazobenzodiazepines (ImBDs)

2016 ◽  
Vol 358 (8) ◽  
pp. 1309-1321 ◽  
Author(s):  
V. Murugesh ◽  
Battu Harish ◽  
Minam Adiseshu ◽  
Jagadeesh Babu Nanubolu ◽  
Surisetti Suresh
Keyword(s):  
Reaction Synthesis ◽  
Van Leusen Reaction

scholarly journals Isonitrile-Based Multicomponent Synthesis of β-Amino Boronic Acids as β-Lactamase Inhibitors

Antibiotics ◽  
2020 ◽  
Vol 9 (5) ◽  
pp. 249 ◽  
Author(s):  
Emanuele Bassini ◽  
Stefano Gazzotti ◽  
Filomena Sannio ◽  
Leonardo Lo Presti ◽  
Jacopo Sgrignani ◽  
...  
Keyword(s):  
Multicomponent Reactions ◽  
Inhibitory Concentration ◽  
Binding Mode ◽  
Antimicrobial Activities ◽  
X Ray Diffraction ◽  
Multicomponent Synthesis ◽  
X Ray ◽  
Class D ◽  
11B Nmr ◽  
Van Leusen Reaction

The application of various isonitrile-based multicomponent reactions to protected (2-oxoethyl)boronic acid (as the carbonyl component) is described. The Ugi reaction, both in the four components and in the four centers–three components versions, and the van Leusen reaction, proved effective at providing small libraries of MIDA-protected β-aminoboronic acids. The corresponding free β-aminoboronic acids, quantitatively recovered through basic mild deprotection, were found to be quite stable and were fully characterized, including by 11B-NMR spectroscopy. Single-crystal X-ray diffraction analysis, applied both to a MIDA-protected and a free β-aminoboronic acid derivative, provided evidence for different conformations in the solid-state. Finally, the antimicrobial activities of selected compounds were evaluated by measuring their minimal inhibitory concentration (MIC) values, and the binding mode of the most promising derivative on OXA-23 class D β-lactamase was predicted by a molecular modeling study.

ChemInform Abstract: Synthesis of 2,5-Diaryloxazoles Through van Leusen Reaction and Copper-Mediated Direct Arylation.

ChemInform ◽  
2009 ◽  
Vol 40 (41) ◽  
Author(s):  
Tomoki Yoshizumi ◽  
Tetsuya Satoh ◽  
Koji Hirano ◽  
Daisuke Matsuo ◽  
Akihiro Orita ◽  
...  
Keyword(s):  
Direct Arylation ◽  
Van Leusen Reaction

scholarly journals Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles

2014 ◽  
Vol 10 ◽  
pp. 2222-2229 ◽  
Author(s):  
Ivana Šagud ◽  
Simona Božić ◽  
Željko Marinić ◽  
Marija Šindler-Kulyk
Keyword(s):  
Silica Gel ◽  
Ring Opening ◽  
Spectroscopic Methods ◽  
Intramolecular Cycloaddition ◽  
Wittig Reactions ◽  
Van Leusen Reaction ◽  
Oxazoline Derivatives

Novel cis/trans-4- and cis/trans-5-(2-vinylstyryl)oxazoles have been synthesized by Wittig reactions from the diphosphonium salt of α,α’-o-xylene dibromide, formaldehyde and 4- and 5-oxazolecarbaldehydes, respectively. In contrast, trans-5-(2-vinylstyryl)oxazole has been synthesized by the van Leusen reaction from trans-3-(2-vinylphenyl)acrylaldehyde which is prepared from o-vinylbenzaldehyde and (formylmethylene)triphenylphosphorane. The 4- and 5-(2-vinylstyryl)oxazoles afford, by photochemical intramolecular cycloaddition, diverse fused oxazoline-benzobicyclo[3.2.1]octadienes, which are identified and characterized by spectroscopic methods. The photoproducts formed are relatively unstable and spontaneously or on silica gel undergo oxazoline ring opening followed by formation of formiato- or formamido-benzobicyclo[3.2.1]octenone derivatives. On irradiation of 4-(2-vinylstyryl)oxazole small quantities of electrocyclization product, 4-(1,2-dihydronaphthalen-2-yl)oxazole, are isolated and spectroscopically characterized.

scholarly journals Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1594 ◽  
Author(s):  
Xunan Zheng ◽  
Wei Liu ◽  
Dawei Zhang
Keyword(s):  
Nitrogen Atom ◽  
Oxygen Atom ◽  
Biological Activities ◽  
Heterocyclic Ring ◽  
Recent Advances ◽  
Medicinal Compounds ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Oxazole Derivatives ◽  
Van Leusen Reaction

Oxazole compounds, including one nitrogen atom and one oxygen atom in a five-membered heterocyclic ring, are present in various biological activities. Due to binding with a widespread spectrum of receptors and enzymes easily in biological systems through various non-covalent interactions, oxazole-based molecules are becoming a kind of significant heterocyclic nucleus, which have received attention from researchers globally, leading them to synthesize diverse oxazole derivatives. The van Leusen reaction, based on tosylmethylisocyanides (TosMICs), is one of the most appropriate strategies to prepare oxazole-based medicinal compounds. In this review, we summarize the recent advances of the synthesis of oxazole-containing molecules utilizing the van Leusen oxazole synthesis from 1972, aiming to look for potential oxazole-based medicinal compounds, which are valuable information for drug discovery and synthesis.

The use of 5-hydroxymethylfurfural towards fine chemicals: Synthesis and direct arylation of 5-HMF-based oxazoles.

Synlett ◽  
2020 ◽  
Author(s):  
Rafael da Rosa ◽  
Lucie Grand ◽  
Eloir Schenkel ◽  
Lilian Sibelle Campos Bernardes ◽  
Maïwenn Jacolot ◽  
...  
Keyword(s):  
Late Stage ◽  
Fine Chemicals ◽  
Direct Arylation ◽  
Platform Chemical ◽  
Palladium Catalyzed ◽  
Oxazole Derivative ◽  
Van Leusen Reaction ◽  
Electron Withdrawing Substituents

5-hydroxymethylfurfural (5-HMF) is a renewable platform chemical used as a source for obtaining diverse fine chemicals. In this letter, we report the synthesis of 5-HMF-based oxazole compounds. While 5-HMF could be easily converted to the oxazole derivative through the Van Leusen reaction, the direct arylation step needed to access the final compounds was problematic at first. After optimization, a palladium-catalyzed procedure has been developed and used for the synthesis of a series of thirty three derivatives. This article reports an extension of the late-stage CH arylation reaction as an application to the oxazole platform derived from biosourced 5-HMF. The challenges in the preparation of the derivatives containing some electron-withdrawing substituents were overcome by the use of a palladium-free method.

ChemInform Abstract: Tandem Copper-Catalyzed N-Arylation-Condensation and van Leusen Reaction: Synthesis of 1,4-Benzodiazepines and Imidazobenzodiazepines (ImBDs).

ChemInform ◽  
2016 ◽  
Vol 47 (37) ◽  
Author(s):  
V. Murugesh ◽  
Battu Harish ◽  
Minam Adiseshu ◽  
Jagadeesh Babu Nanubolu ◽  
Surisetti Suresh
Keyword(s):  
Reaction Synthesis ◽  
Van Leusen Reaction
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