, 6-(1-Indol-4-yl)-8-methoxy-1-methyl-4-[1,2,4]triazolo[4,3-][1,4]benzodiazepine-4-acetic acid methyl ester, has been synthesized on a near-gram scale in seven steps with notable improvements in the reported poor-yielding last two steps enabling this key chemical probe compound to be available for researchers.
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http://dx.doi.org/10.1021/acsomega.7b00780 | DOI Listing |
Org Lett
January 2025
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. China.
The azahelicenes are structurally fascinating and practically useful chiral scaffolds, but their synthesis, especially in a catalytically asymmetric manner, is rather challenging. Herein, we report a CPA-catalyzed transfer hydrogenation process, which enables a rapid kinetic resolution of aza[6]helicenes. The established strategy provides facile access to enantioenriched aza[6]helicenes and tetrahydro[6]helicenes from easily available starting materials.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. China.
A strategy for trifluoroacetylation of quinoxaline-2(1)-ones has been investigated. This strategy employs masked trifluoroacyl reagents to obtain trifluoroacetylated quinoxaline-2(1)-ones under metal-, catalyst-, and light-free conditions. This approach is distinguished by its functional group compatibility and tolerance, as well as the simplicity of the experimental process, making it suitable for gram-scale synthesis.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
State Key Laboratory of New Pharmaceutical Preparations and Excipients, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Materials Science, Hebei University, Baoding, Hebei, 071002, P. R. China.
Herein, we describe a visible-light-mediated selenocyclization of -vinylanilides with diselenides, which provides a mild and effective method for the synthesis of selenylated 4-3,1-benzoxazines. This reaction proceeds under metal-free conditions, without the need for a chemical oxidant or a controlled O atmosphere and shows a broad substrate scope with yields of up to 98%. Additionally, the process is easily scalable to the gram scale.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, Xi'an Jiaotong University, Xi'an 710049, China.
We describe an efficient acyl esterification method for alkenes utilizing acyloxime esters as bifunctional reagents featuring radical acylation and congested C-O bond formation. This approach is characterized by mild photoredox conditions, high step and atom economy, a broad substrate scope, and excellent regioselectivity. A variety of valuable α-acyl hindered alcohol esters, including those obtained via gram-scale synthesis and late-stage functionalization of pharmaceutical molecules, were presented, demonstrating its synthetic potential and practicability.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, Guangxi, P. R. China.
We present a mild and efficient method for the arylation of N-H heteroarenes using a low-loading Pd/keYPhos catalyst (0.8 mol%). This approach employs inexpensive and structurally diverse aryl chlorides as electrophiles in reactions with indoles, pyrroles, and carbazole, enabling the construction of a wide range of -arylated products.
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