- A segmented flow platform for on-demand medicinal chemistry and compound synthesis in oscillating droplets
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We report an automated flow chemistry platform that can efficiently perform a wide range of chemistries, including single/multi-phase and single/multi-step, with a reaction volume of just 14 μL. The breadth of compatible chemistries is successfully demonstrated and the desired products are characterized, isolated, and collected online by preparative HPLC/MS/ELSD.
- Hwang, Ye-Jin,Coley, Connor W.,Abolhasani, Milad,Marzinzik, Andreas L.,Koch, Guido,Spanka, Carsten,Lehmann, Hansjoerg,Jensen, Klavs F.
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supporting information
p. 6649 - 6652
(2017/07/10)
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- Utilization of carbon disulfide as a powerful building block for the synthesis of 2-aminobenzoxazoles
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This protocol describes a novel, mild and convenient route to afford 2-aminobenzoxazoles in high yields, and represents a significant advance towards an environmentally friendly strategy. Aliphatic amines are made to react with carbon disulfide to provide intermediate dithiocarbamates (DTC), which in the presence of 2-aminophenol, subsequently undergo successive intermolecular nucleophilic attack and desulfurization to produce 2-aminobenzoxazoles within 3 h.
- Guntreddi, Tirumaleswararao,Allam, Bharat Kumar,Singh, Krishna Nand
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p. 9875 - 9880
(2013/09/02)
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- Iodine-catalyzed amination of benzoxazoles: A metal-free route to 2-aminobenzoxazoles under mild conditions
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A facile metal-free route of oxidative amination of benzoxazole by activation of C-H bonds with secondary or primary amines in the presence of catalytic iodine in aqueous tert-butyl hydroperoxide proceeds smoothly at ambient temperature (Figure presented) under neat reaction condition to furnish the high yield of the aminated product. This user-friendly method to form C-N bonds produces tertiary butanol and water as the byproduct, which are environmentally benign. The application of the methodology is demonsrated by synthesizing therapeutically active benzoxazoles.
- Lamani, Manjunath,Prabhu, Kandikere Ramaiah
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experimental part
p. 7938 - 7944
(2011/11/30)
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- Synthesis of 2-aminobenzoxazoles using tetramethyl orthocarbonate or 1,1-dichlorodiphenoxymethane
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The synthesis of 2-aminobenzoxazoles can be readily achieved by two versatile, one-pot procedures utilizing commercially available tetramethyl orthocarbonate or 1,1-dichlorodiphenoxymethane, an amine, and an optionally substituted 2-aminophenol. The reactions were conducted under mild conditions and provided 2-aminobenzoxazoles in modest to excellent yields. A variety of amines and substituted 2-aminophenols were used to investigate the scope of the reactions.
- Cioffi, Christopher L.,Lansing, John J.,Yueksel, Hamza
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supporting information; experimental part
p. 7942 - 7945
(2011/02/23)
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- SYNTHESIS OF 2-AMINOBENZOXAZOLE COMPOUNDS
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A method for forming an optionally substituted 2-aminobenzoxazole compound includes: contacting an optionally substituted 2-aminophenol compound with (1) an amine of the formula NHR2R3, wherein R2 and R3 are each independently selected from H, an optionally substituted alkyl group or an optionally substituted aryl group, or R2 and R3, taken together with the nitrogen atom to which they are attached, form an optionally substituted heterocyclic ring; and (2) a reactant selected from the group consisting of: (a) C(OR)4, wherein R represents an alkyl group; (b) C(OAr)4, wherein Ar represents an aryl group; and (c) CCl2(OAr)2, wherein Ar represents an aryl group, in combination with a base; thereby forming the optionally substituted 2-aminobenzoxazole compound.
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Page/Page column 8
(2010/05/13)
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