496865-35-1Relevant articles and documents
SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride
Yamanushkin, Pavel,Kaya, Kemal,Feliciano, Mark Aldren M.,Gold, Brian
supporting information, p. 3868 - 3873 (2022/02/23)
Click reactions have transformed the molecular sciences. Augmenting cycloaddition reactions, sulfur(VI) fluoride exchange (SuFEx) chemistry has diversified the landscape of molecular assembly. Herein, we report a facile strategy to access SuFExable NH-pyrazoles via strain and catalyst-free 1,3-dipolar cycloadditions of stabilized diazo compounds under mild conditions. Subsequent SuFEx proceeds efficiently with various N- and O-nucleophiles. Access to SuFExable NH-pyrazoles-a class of compounds containing two common pharmacophores-enables future opportunities within drug discovery, chemical biology, materials chemistry, and related fields.
B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether
Karaluka, Valerija,Lanigan, Rachel M.,Murray, Paul M.,Badland, Matthew,Sheppard, Tom D.
supporting information, p. 10888 - 10894 (2015/11/17)
The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.
1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes
Kissane, Marie,Lawrence, Simon E.,Maguire, Anita R.
supporting information; experimental part, p. 2735 - 2748 (2010/08/21)
2-Thio-3-chloroacrylamides undergo 1,3-dipolar cycloadditions with diazoalkanes leading to a series of novel pyrazolines and pyrazoles. The mechanistic and synthetic features of the cycloadditions to the 2-thio-3-chloroacrylamides at both the sulfide and sulfoxide levels of oxidation are rationalised on the basis of the nature of the substituents.
