Browsing by Author "Chen, Chan-Yu"

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Design and Synthesis of New Biprivileged Molecular Scaffolds: Indolo-Fused Benzodiazepinyl/quinoxalinyl benzimidazoles
(2012-06-01)
Barve, Indrajeet J.
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Chen, Chan-Yu
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Salunke, Deepak B.
;
Chung, Wen-Sheng
;
Sun, Chung-Ming
The present article describes the design and synthesis of new biprivileged molecular scaffolds with diverse structural features. Commercially available, simple heterocyclic building blocks such as 4-fluoro-3-nitrobenzoic acid, 2-chloro-3-nitrobenzoic acid, and indoline were utilized for the synthesis of the novel heterocycles. PictetSpengler-type condensation was used as a key step to construct tetracyclic indolo-benzodiazepines and indolo-quinoxalines linked with substituted benzimidazoles. Analysis of single crystals of representative compounds showed that these molecular skeletons have the potential to present various substituents with distinct three-dimensional orientations.
Novel ionic liquid supported-multicomponent reaction toward chimeric bis-heterocycles
(2012-08-01)
Chen, Chih-Hau
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Chen, Chan-Yu
;
Lin, Po-Tsung
;
Sun, Chung-Ming
;
應用化學系
A novel multicomponent reaction between IL-anchored 2-aminobenzoimidazoles, aldehydes, and electron-deficient dienophiles has been explored. The strategy was utilized to develop a rapid parallel synthesis for novel bis-heterocyclic skeleton of benzimidazole-linked dihydropyrimidine on an ionic liquid support. This multicomponent reaction is compatible with a wide range of substrates and furnishes the new chimeric scaffolds with high purity and excellent yields. Use of the ionic liquid as a soluble support facilitates purification by simple precipitation along with advantages like high loading capacity, homogeneous reaction conditions, and monitoring of the reaction progress by conventional NMR spectroscopy.
One-Pot Three-Component Synthesis of 2-Imino-1,3-Thiazolines on Soluble Ionic Liquid Support
(2016-10)
Chen, Chan-Yu
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Barve, Indrajeet J.
;
Sun, Chung-Ming
;
應用化學系
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Department of Applied Chemistry
An efficient one-pot, three-component synthesis of 2-imino-1,3-thiazolidines and 2-imino-1,3-thiazolines using ionic liquid-tethered 2-aminobenzimidazoles was reported. The protocol includes reaction of ionic liquid attached 2-aminobenzimidazoles with isothiocyanates to afford isothioureas, followed by its base induced inter and intramolecular nucleophilic displacement reactions with 1,2-dichloroethane (EDC) which results in thiazolidine ring formation. In the next to the last step, the ionic liquid support was removed by methanolysis to deliver 2-imino-1,3-thiazolidines, which were sequentially oxidized with manganese(III) triacetate to yield 2-imino-1,3-thiazolines. The salient feature of this method is the use of 1,2-dichloroethane as a synthetic equivalent for alpha-haloketone to avoid the use of toxic halogenating reagents.