CuH-catalyzed diasterospecific synthesis of 3-hydroxyindolines and 2-aryl-3H-indol-3-ones have been developed from -alkynylnitroarenes in the presence of hydrosilane as the reductant. The protocol employs nitro as both nitrogen and oxygen sources for the intramolecular simultaneous construction of C-N and C-O bonds.
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CuH-Catalyzed Synthesis of 3-Hydroxyindolines and 2-Aryl-3H-indol-3-ones from -Alkynylnitroarenes, Using Nitro as Both the Nitrogen and Oxygen Source.
Org Lett
August 2019
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology, Guangzhou , People's Republic of China , 510640.
CuH-catalyzed diasterospecific synthesis of 3-hydroxyindolines and 2-aryl-3H-indol-3-ones have been developed from -alkynylnitroarenes in the presence of hydrosilane as the reductant. The protocol employs nitro as both nitrogen and oxygen sources for the intramolecular simultaneous construction of C-N and C-O bonds.
View Article and Find Full Text PDF[The chemistry of pericyclic reactions and their application to syntheses of heterocyclic compounds].
Yakugaku Zasshi
September 2003
Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose 204-8588, Japan.
Diels-Alder reactions of benzylidenecyanomethyl-1,3-benzothiazoles 17 and -1,3-benzoxazoles 18 as 1-aza-1,3-butadienes are described. The dienes 17 and 18 featuring stabilized imine moieties in the form of heteroaromatic rings react with both electron-deficient and electron-rich dienophiles to give corresponding cycloadducts regioselectively. The cycloadditions of the intramolecular systems 34c,d and 35c,d proceeded smoothly via the exo-transition state, stereoselectively affording polycyclic compounds 36c,d and 37c,d in good to excellent yields.
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