497066-41-8Relevant academic research and scientific papers
Aromatic enamide/ene metathesis toward substituted indoles and its application to the synthesis of indomethacins
Kasaya, Yayoi,Hoshi, Kosuke,Terada, Yukiyoshi,Nishida, Atsushi,Shuto, Satoshi,Arisawa, Mitsuhiro
experimental part, p. 4606 - 4613 (2009/12/27)
A. steric and electronic effect: on enamide/ene metathesis, a novel preparation of 2-substituted indoles and 3-substituted indoles using enamide-ene metathesis as a key reaction, and its application to the synthesis of indoniethacin are described. Wiley-VCH Verlag GmbH & Co. KGaA.
Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles
Arisawa, Mitsuhiro,Terada, Yukiyoshi,Takahashi, Kazuyuki,Nakagawa, Masako,Nishida, Atsushi
, p. 4255 - 4261 (2007/10/03)
A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.
Cycloisomerization promoted by the combination of a ruthenium-carbene catalyst and trimethylsilyl vinyl ether, and its application in the synthesis of heterocyclic compounds: 3-Methylene-2,3-dihydroindoles and 3-methylene-2,3- dihydrobenzofurans
Terada, Yukiyoshi,Arisawa, Mitsuhiro,Nishida, Atsushi
, p. 4063 - 4067 (2007/10/03)
Substituted N and O heterocycles have been synthesized by the cycloisomerization of dienes using a ruthenium-carbene catalyst. The products obtained with and without trimethylsilyl vinyl ether differ (see scheme, Cy = cyclohexyl, Mes = 2,4,6-trimethylphenyl, Ts = p-toluenesulfonyl).
Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis
Arisawa, Mitsuhiro,Terada, Yukiyoshi,Nakagawa, Masako,Nishida, Atsushi
, p. 4732 - 4734 (2007/10/03)
Aruthenium complex, generated from the Grubbs carbene catalyst with vinyloxytrimethylsilane, catalyzed the isomerization of terminal alkenes RCH2-CH=CH2 to internal alkenes RCH=CH-CH3. Application of this olefin isomerization to 2-(N-allylamino)styrene gave the corresponding enamines, which were converted into indoles by a standard ring-closing metathesis, see scheme (Ts = tosyl).
