The umpolung of -tosylhydrazones was reported for the first time. Synthesis of -cyano tosylhydrazones was developed, and various -cyano tosylhydrazones were prepared in good yields. An umpolung -tosylhydrazones mechanism was proposed. Meanwhile, the [3,3]-sigmatropic rearrangement of -cyano tosylhydrazones was examined, and the corresponding 2-aminoimidazoles were given.
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Umpolung of -Tosylhydrazones: Synthesis of -Cyano Tosylhydrazones and Their [3,3]-Sigmatropic Rearrangement to 2-Aminoimidazoles.
J Org Chem
December 2024
School of Pharmacy, Lanzhou University, Lanzhou 730000, P. R. China.
The umpolung of -tosylhydrazones was reported for the first time. Synthesis of -cyano tosylhydrazones was developed, and various -cyano tosylhydrazones were prepared in good yields. An umpolung -tosylhydrazones mechanism was proposed.
View Article and Find Full Text PDFCascade Reaction of Arylboronic Acids and 2'-Cyano-biaryl-2-aldehyde N-Tosylhydrazones: Access to Functionalized 9-Amino-10-arylphenanthrenes.
J Org Chem
January 2019
School of Chemistry and Chemical Engineering, the Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan , Shihezi University, Shihezi City , 832004 , China.
An efficient, general, and convenient protocol for the synthesis of functionalized 9-amino-10-arylphenanthrene derivatives using a catalyst-free cascade reaction of arylboronic acids and 2'-cyano-biaryl-2-aldehyde N-tosylhydrazones is described. The synthesis was carried out via simple experimental conditions using NaCO in 1,4-dioxane as a solvent. Moreover, the 9-amino-10-arylphenanthrene compounds were also obtained on a gram scale and further derivatized to synthesize the fused phenanthrene derivatives.
View Article and Find Full Text PDFCopper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center.
Chem Sci
October 2017
Key Laboratory of Functional Molecular Engineering of Guangdong Province , School of Chemistry and Chemical Engineering , South China University of Technology, Guangzhou 510640 , China . Email: ; Email:
Sulfur-containing nitriles have important research value in the life sciences due to their diverse biological activities resulting from the sulfur and cyano functional groups. Herein, a copper-catalyzed cyanothiolation of -tosylhydrazones with thiocyanates to generate α-arylthioalkanenitriles bearing sulfur-substituted quaternary carbon center atoms has been described. This novel protocol involves the procedure of copper carbene species promoting S-CN bond cleavage and C-CN/C-S bond reconstruction to introduce both sulfur and cyano groups onto a single carbon center.
View Article and Find Full Text PDFStereoselective Domino Carbocyclizations of γ- and δ-Cyano-N-tosylhydrazones with Alkenylboronic Acids with Formation of Two Different C(sp(3))-C(sp(2)) Bonds on a Quaternary Stereocenter.
J Am Chem Soc
September 2016
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo , c/Julián Clavería 8, 33006 Oviedo, Spain.
A novel strategy for the synthesis of functionalized carbocycles is defined, through the cascade carbocyclization of alkenylboronic acids with δ- or γ-cyano-N-tosylhydrazones. In the reaction, two C(sp(3))-C(sp(2)) bonds are formed on the former hydrazonic carbon generating an all-carbon quaternary stereocenter, and leading to cyclic ketones featuring an alkenyl side chain with complete diastereoselectivity. The processes are conducted under very simple experimental conditions, only in the presence of K2CO3, in 1,4-dioxane as solvent and under microwave irradiation, and have been applied for the synthesis of a wide structural variety of fused cyclopentanones and cyclohexanones.
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J Am Chem Soc
February 2001
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
A series of tosylhydrazone derivatives of exo-6-substituted bicylo[2.2.2]octan-2-ones have been prepared.
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