Ruthenium complex catalyzed n-heterocyclization. Indoles from aminoarenes and glycols.

Tsuji, Yasushi; Huh, Keun-Tae; Watanabe, Yoshihisa

doi:10.1016/s0040-4039(00)84023-x

Cited by 55 publications

(11 citation statements)

References 4 publications

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“…1.2 芳胺为底物的环化反应 1.2.1 芳胺与二元醇的环化反应由芳胺和二元醇通过氧化环化一步合成吲哚环化合物, 该方法不仅原料价廉、工艺简单, 而且催化剂高效、无毒. 此反应最早于 1986 年由 Watanabe 等 [34] 报道, 他们在 3-(三苯基膦)二氯化铑催化条件下, 温度在 180 ℃时环化脱水得到 2,3-二取代吲哚, 收率在 50%左右. 2010 年, Madsen 等 [35] 报道了在铱配合物或者三氯化铑水合物催化条件下合成 2,3-二取代吲哚, 这是一种最直接和原子经济性的方法, 副产物只有水和氢气(Eq.…”

Section: 在固相中的环化反应unclassified

Progress in the Synthesis of 2,3-Disubstituted Indole by Cyclization

梁亭¹,

李军²,

刘宇³

et al. 2016

Chin. J. Org. Chem.

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In recent years, there are many reports about the synthesis of 2,3-disubstituted indole by cyclization. Most of these approaches are catalyzed by different transition metals and metal-free catalysis conditions using phenylnydrazines, anilines and nitrobenzenes as main substrates. These methods have been a powerful strategy to obtain 2,3-disubstituted indoles. The recent progress of the synthesis of 2,3-disubstituted indoles by cyclization with the different substrates systems is summarized.

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Section: 在固相中的环化反应unclassified

Progress in the Synthesis of 2,3-Disubstituted Indole by Cyclization

梁亭¹,

李军²,

刘宇³

et al. 2016

Chin. J. Org. Chem.

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“…99,100 We found that benzo[h]quinolines and benzoindole derivatives could be synthesized in high yields by the iridiumcatalyzed direct cyclization of naphthylamines with 1,3-and 1,2-diols, respectively. 101 As an example, using the preparation of benzo[h]quinoline, a mixture of 1-naphthylamine (75) (5 mmol) and propane-1,3-diol (76) (77) in 96% isolated yield (Scheme 33).…”

Section: Synthesis Of Benzo[h]quinolines and Benzoindole Derivatives mentioning

confidence: 99%

“…As an alternative methodology for the synthesis of quinoline and indole derivatives, the ruthenium-catalyzed Ncyclization of anilines with diols has been reported. 99,100 We found that benzo[h]quinolines and benzoindole derivatives could be synthesized in high yields by the iridiumcatalyzed direct cyclization of naphthylamines with 1,3and 1,2-diols, respectively. 101 As an example, using the preparation of benzo[h]quinoline, a mixture of 1-naphthylamine ( 75 (77) in 96% isolated yield (Scheme 33).…”

Section: Synthesis Of Benzo[h]quinolines and Benzoindole Derivatives From Naphthylamines And Diolsmentioning

confidence: 99%

Iridium-Catalyzed Reactions Involving Transfer Hydrogenation, Addition, N-Heterocyclization, and Alkylation Using Alcohols and Diols as Key Substrates

Obora¹,

Ishii²

2010

Synlett

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This account gives an overview of iridium-catalyzed reactions developed by our group using mainly alcohols and diols as substrates. In the presented reactions, the iridium catalyst serves as a hydrogen acceptor from the alcohols giving iridium hydride, which is a key transient species. Herein, we report hydrogenation, alkylation, esterification, N-heterocyclization, and coupling reactions using alcohols and diols as reagents.

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“…The Watanabe synthesis between substituted N-alkylanilines and 1,2-diols develops through an oxidative cyclization but requires the use of expensive ruthenium-based metal catalysts, dioxane as a solvent and fairly high temperatures (180 °C). [14] When N-methylaniline was reacted with 1,2-propanediol an equimolar mixture of 1,2-and 1,3-dimethyl indole was obtained, [15] showing a limited selectivity and reducing the usefulness of the approach. The Nenitzescu synthesis, named after its discoverer, [16] permits to obtain substituted 5-hydroxyindoles starting from 1,4-benzoquinone and an enamine (typically 3-aminocrotonates) by the reaction at reflux.…”

Section: Introductionmentioning

confidence: 99%