Recent advances in C–H functionalization of 2<i>H</i>-indazoles

Yang, Zixian; Yu, Jin‐Tao; Pan, Changduo

doi:10.1039/d2ob01463g

Cited by 26 publications

(15 citation statements)

References 105 publications

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“…With this consideration, we chose the addition with the Grignard reagents (first step) and subsequent dehydrogenative oxidation (second step) protocol, rather than the direct C(sp 2 )–H activation and functionalization protocol, because the latter always requires the use of noble transition metals and is operationally plagued by the necessity of numerous additives and harsh conditions. 20 21 By using a two-step sequence of Grignard addition and DDQ dehydrogenation, we came up with an efficient method for synthesizing 11-aryldibenzooxa/thiazepines via the late-stage arylation strategy (Scheme 1b, v ). The reactions are performed either by a two-step procedure without purifying the intermediates or directly in a one-pot procedure, giving 11-aryldibenzooxa/thiazepines in excellent yields in a convenient fashion.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Late-Stage Two-Step C11–H Arylation of Dibenzooxa/thiazepines

Yang¹,

et al. 2023

Synthesis

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A practical and efficient synthesis of 11-aryldibenzooxa/thiazepines is achieved, via a late-stage and two-step C11-H arylation of simple dibenzooxa/thiazepines. The adoption of Grignard addition and DDQ dehydrogenation allows for opera-tionally simple and chemically reliable, and step-efficient and high-yielding transformations. The two-step and one-pot procedures provide excellent yields. The gram-scale experiment demonstrates the promising synthetic potentials in large-scale applications, and the advantages of this method are also highlighted in the efficient synthesis of an H460TaxR inhibitor.

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Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Late-Stage Two-Step C11–H Arylation of Dibenzooxa/thiazepines

Yang¹,

et al. 2023

Synthesis

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“…8 In view of the importance of 2 H -indazoles and their derivatives, several attempts have been made to synthesize and functionalize indazoles. 9…”

Section: Introductionmentioning

confidence: 99%

Silylation of 2H-indazoles by photoinduced hydrogen atom transfer catalysis

Das,

Hajra

2024

Org. Biomol. Chem.

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“…Enantioselective catalysts, such as chiral transition metal catalysts developed initially by Knowles, Noyori, and Sharpless, or organocatalysts developed by List and MacMillan, introduce a chiral environment, which induces the formation of an enantiopure product, and due to the importance of these discoveries, both concepts were awarded with the Nobel prize in 2001 and 2021, respectively [7] . These breakthroughs finally led to the development of catalysts for synthesizing chiral pharmaceutical compounds [6a] . While enantioselective synthesis is a critical process for industry, the recognition and separation of pharmaceutical compounds are also essential processes in this context.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective recognition, synthesis, and separation of pharmaceutical compounds at chiral metallic surfaces

Suwankaisorn,

Aroonratsameruang,

Kuhn

et al. 2024

ChemMedChem

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The development of new pharmaceutical compounds is challenging because most of them are based on enantiopure chiral molecules, which exhibit unique properties for therapy. However, the synthesis of pharmaceutical compounds in the absence of a chiral environment naturally leads to a racemic mixture. Thus, to control their synthesis, an asymmetric environment is required, and chiral homogeneous catalysts are typically used to synthesize enantiopure pharmaceutical compounds (EPC). Nevertheless, homogeneous catalysts are difficult to recover after the reaction, generating additional problems and costs in practical processes. Thus, the development of chiral heterogeneous catalysts is a timely topic. In a more general context, such chiral materials cannot only be used for synthesis, but also to recognize and separate enantiomers. In the frame of these different challenges, we give in this review a short introduction to strategies to extrinsically and intrinsically modify heterogeneous metal matrixes for the enantioselective synthesis, recognition, and separation of chiral pharmaceutical compounds.

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Recent advances in C–H functionalization of 2H-indazoles

Abstract: 2H-Indazoles are one class of the most important nitrogen-containing heterocyclic compounds. The 2H-indazole motif is widely present in bioactive natural products and drug molecules that exhibiting distinctive bioactivities. Therefore, much...

Cited by 26 publications

References 105 publications

Late-Stage Two-Step C11–H Arylation of Dibenzooxa/thiazepines

Late-Stage Two-Step C11–H Arylation of Dibenzooxa/thiazepines

Silylation of 2H-indazoles by photoinduced hydrogen atom transfer catalysis

Enantioselective recognition, synthesis, and separation of pharmaceutical compounds at chiral metallic surfaces

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