- Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine
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Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.
- Wu, Weiping,Fan, Shuaixin,Li, Tielei,Fang, Lili,Chu, Benfa,Zhu, Jin
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supporting information
p. 5652 - 5657
(2021/08/01)
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- Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles
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Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is
- Zhang, Lei,Chen, Junyu,Chen, Xiahe,Zheng, Xiangyun,Zhou, Jian,Zhong, Tianshuo,Chen, Zhiwei,Yang, Yun-Fang,Jiang, Xinpeng,She, Yuan-Bin,Yu, Chuanming
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supporting information
p. 7415 - 7418
(2020/07/15)
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- A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles
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A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.
- Zhou, Shuguang,Wang, Jinhu,Zhang, Feifei,Song, Chao,Zhu, Jin
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supporting information
p. 2427 - 2430
(2016/06/09)
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- Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant
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A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.
- Zhou, Shuguang,Wang, Jinhu,Chen, Pei,Chen, Kehao,Zhu, Jin
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supporting information
p. 14508 - 14512
(2016/10/03)
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- Hydrazinocarbonyl-thieno[2,3-C]pyrazoles, Process for Preparing Them, Compositions Containing Them and Use Thereof
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The present invention concerns hydrazinocarbonyl-thieno[2,3-c]pyrazoles of formula (I): wherein R1, R3, R4, are R5 are as defined in the disclosure; their preparation method, compositions containing the same and their use for the treatment of pathological conditions, in particular as anticancer agents.
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- MECHANISM OF THE FISCHER INDOLE SYNTHESIS. QUANTUM-CHEMICAL INTERPRETATION OF THE REARRANGEMENT OF SUBSTITUTED CYCLOHEXANONE ARYLHYDRAZONES TO TETRAHYDROCARBAZOLES
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Calculations of a number of model structures within the scheme of Fischer indole synthesis were made on the basis of a bonding variant of perturbation theory in the self-consistent-field (SCF) MO LCAO method.A quantum-chemical interpretation of the effect of substituents on the course of the thermal process is given.The kinetics of the thermal and acid-catalyzed indolization of substituted cyclohexanone arylhydrazones to tetrahydrocarbazoles were studied by spectrophotometry.It was shown that the experimental data are in satisfactory agreement with the calculated values. It was concluded that a concerted mechanism ( a -sigma-tropic shift) for the step involving the formation of a carbon-carbon bond in the Fischer reaction is preferred.
- Visotskii, Yu. B.,Przheval'skii, N. M.,Zemskii, B. P.,Grandberg, I. I.,Kostromina, L. Yu.
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p. 713 - 722
(2007/10/02)
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