Synthesis of 3-Substituted Indoles by a Palladium-Assisted Reaction

Kasahara, Akira; Izumi, Taeko; Murakami, Satoshi; Yanai, Hiroshi; Takatori, Masayuki

doi:10.1246/bcsj.59.927

Cited by 71 publications

(17 citation statements)

References 3 publications

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“…An example is the reaction of 2-bromoaniline with acrylates (activated olefin). 150 In contrast to the difficult intermolecular reaction, the intramolecular aminopalladation 18 proceeds more easily. Pioneering work came from Hegedus and coworkers who reported the synthesis of indole and substituted indoles such as 2-methylindole by palladium-catalyzed cyclization of o-vinylanilines or o-allylanilines in the presence of benzoquinone as reoxidant (Scheme 22).…”

Section: Aminations Catalyzed By Transition Metals a Palladium-cataly...mentioning

confidence: 99%

Metal-Initiated Amination of Alkenes and Alkynes

1998

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ContentsI. Introduction 675 II. Mechanism and Coordination Chemistry 676 1. Activation of the Olefin 677 a. Stoichiometric Use of Transition Metals 677 b. Making the Reaction Catalytic 679 2. N−H Activation by Alkali Metals 680 3. Activation of the N−H Bond by Early Transition Metals, Lanthanides, and Actinides 681 4. Activation of the N−H Bond by Late Transition Metals 684 III. Synthetic Applications of Catalytic Aminations 686 1. Aminations Catalyzed by Zeolites 686 2. Aminations Assisted by Alkali Metals 686 a. Ethylene 686 b. Aliphatic Olefins 687 c. Styrenes 688 d. 1,3-Butadienes 689 3. Aminations Catalyzed by Transition Metals 690 a. Palladium-Catalyzed Aminations of Olefins 690 b. Other Catalytic Oxidative Aminations of Olefins 693 c. Amination of Allenes 693 d. Intramolecular Amination of Alkynes 694 e. Intramolecular Amination of Alkenes 695 f. Tandem Cyclization Reactions of Aminoalkynes and -alkenes 697 g. Intermolecular Hydroamination Reactions 698 IV. Summary and Conclusions 699 V. Acknowledgments 700 VI. References 700

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Section: Aminations Catalyzed By Transition Metals a Palladium-cataly...mentioning

confidence: 99%

Metal-Initiated Amination of Alkenes and Alkynes

1998

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“…On the basis of the carbonylative cyclization of related 2-substituted N -(2-haloaryl)-2-propenoates described by Torii et al, we initially used the same reaction conditions [Pd(OAc) 2 , PPh 3 , K 2 CO 3 , DMF, CO (20 atm), 120 °C] for the conversion of 1a , our model system, into the corresponding 2a . However, 2a was isolated only in 5% yield after 24 h along with a 76% yield of the recovered starting material and a 7% yield of indole, derived from the direct palladium-catalyzed cyclization of 1a . − Slightly better results, but still unsatisfactory from a synthetic point of view, were obtained prolonging the reaction time to 72 h ( 2a , 30%; recovered 1a , 53%; indole derivative, 13%).…”

Section: Results and Discussionmentioning

confidence: 99%

Design, Palladium-Catalyzed Synthesis, and Biological Investigation of 2-Substituted 3-Aroylquinolin-4(1H)-ones as Inhibitors of the Hedgehog Signaling Pathway

et al. 2017

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2-Substituted 3-aroylquinolin-4(1H)-ones, prepared through a palladium-catalyzed carbonylative cyclization of N-(2-iodoaryl)enaminones, proved to inhibit efficiently the Hedgehog pathway through direct antagonism of the wild-type and drug-resistant form of the Smoothened receptor. Notably, these compounds repressed the Hh-dependent growth events and the proliferation of tumor cells with aberrant activation of the Hh pathway, which plays a crucial role in development and tumorigenesis.

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“…• C (4 mmHg 3 ). [19] The synthesis of product 2d Prepared as described above using 1d (2.1 g) as the reactant.…”

Section: The Synthesis Of Product 2cmentioning

confidence: 99%

“…[1,2] Skatole with a strong fecal odor has been found naturally in feces, beets, coal and tar and used as a fixative in the manufacture of perfume, but in low concentrations, it has a flowery smell. [3] It is an important element of the high-quality perfume civet. [4] The Heck reaction (also called the Mizoroki-Heck reaction) is an important coupling reaction occurs in the presence of palladium catalyst.…”

Section: Introductionmentioning

confidence: 99%