Cu(OAc)2-catalyzed hydrazination of cyclopropanols and late-stage transformation to 4,5-dihydropyrazoles

Review Chemistry, Multidisciplinary

Direct decarboxylative Giese reactions

David M. Kitcatt et al.

Summary: This review summarizes the recent progress on using carboxylic acids directly as convenient radical precursors for the formation of carbon-carbon bonds.

CHEMICAL SOCIETY REVIEWS (2022)

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Article Chemistry, Organic

Electrophilic Hydrazination of Cyclopropanols Using Azodicarboxylates via Copper(II) Catalysis: An Umpolung Strategy to Access β-Hydrazino Ketone Motifs

Thangeswaran Ramar et al.

Summary: This study demonstrates an umpolung approach to expand synthetic access to bifunctional y-keto hydrazine intermediates, using an electrophilic amination reaction. The reaction proceeds under mild conditions and allows the synthesis of various organic compounds.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Cyclopropenes with Cobalt Homoenolates

Wei Huang et al.

Summary: The synthesis of multi-substituted cyclopropanes with high yields and enantioselectivity was achieved through the catalytic diastereo- and enantioselective hydroalkylation of 3,3-disubstituted cyclopropenes promoted by a chiral phosphine-cobalt complex. The approach allows for the direct introduction of functionalized alkyl groups onto the cyclopropane motif without the need for pre-formation of stoichiometric amounts of organometallic reagents, providing access to enantioenriched cyclopropanes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary

Metal-Catalyzed Transformations of Cyclopropanols via Homoenolates

Yoshiya Sekiguchi et al.

Summary: This review article provides an overview of the development of homoenolate transformations, highlighting the reliable use of siloxycyclopropanes as precursors and the attractive alternative of unprotected cyclopropanols, often catalytically generated, in carbon-carbon and carbon-heteroatom bond-forming reactions. The transformations are classified based on the metals involved in the cyclopropane ring opening.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2021)

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Review Chemistry, Multidisciplinary

Selective Carbon-Carbon Bond Cleavage of Cyclopropanols

Tyler R. McDonald et al.

Summary: The carbon-carbon bond cleavage of cyclopropanols is a research hotspot, involving three main reactivity modes such as homoenolate chemistry, beta-keto radical chemistry, and acid-catalyzed ring-opening. Various methods for the C-C bond cleavage and functionalization of cyclopropanols are summarized, emphasizing their synthetic utility.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

Qi Zhang et al.

Summary: A catalytic asymmetric allylic substitution using copper(I) homoenolates as nucleophiles has been achieved, with high yields and enantioselectivity. The method is applicable to a broad range of substrates and can be extended to the construction of chiral quaternary carbon centers.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Medicinal

Design, synthesis, and SAR study of novel 4,5-dihydropyrazole-Thiazole derivatives with anti-inflammatory activities for the treatment of sepsis

Zhen Zhang et al.

Summary: In this study, a novel compound E26 was designed and synthesized to treat sepsis by inhibiting inflammatory response. Experimental results demonstrated that compound E26 exhibited potent anti-inflammatory activity by suppressing the production of various inflammatory factors through blocking the MAPKs signaling pathway, and showed significant efficacy in a mouse model of sepsis.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

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Article Chemistry, Organic

Nickel-Catalyzed Asymmetric Hydrogenation of Hydrazones

Bowen Li et al.

Summary: An efficient nickel-catalyzed asymmetric hydrogenation of hydrazones to chiral hydrazines has been achieved with high yields and enantiomeric excess. Deuterium labelling experiments showed tautomerization of hydrazone substrates in mixed solvents, while the presence of acids promoted the dissociation of the active nickel catalyst in the catalytic cycle.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Photocatalytic divergent decarboxylative amination: a metal-free access to aliphatic amines and hydrazines

Xianli Shu et al.

Summary: This article presents an invention of a visible light-mediated reaction using abundant carboxylic acids and a commercial diazirine to synthesize nitrogen-containing molecules. This divergent method can rapidly build nitrogen-containing molecule libraries with considerable structural diversity, potentially benefiting studies in chemical biology and drug discovery.

SCIENCE CHINA-CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Photocatalyst- and additive-free site-specific C(sp3)-H hydrazination of glycine derivatives and peptides

Guang-Zu Wang et al.

Summary: A visible light-mediated protocol for site-specific C(sp(3))-H hydrazination of glycine derivatives and peptides with azo compounds has been developed. This reaction proceeds smoothly under photo-irradiation conditions in the absence of any catalysts and additives, providing a convenient method for efficient preparation of unnatural alpha-amino acids and precise modification of short peptides. Mechanism investigations suggest that single electron transfer (SET) and hydrogen atom transfer (HAT) may occur during this transformation.

GREEN CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Rolando Cannalire et al.

Summary: Late stage functionalization is a powerful tool for accelerating the identification of structure-activity relationships and optimizing ADME profiles of drugs. Visible-light photocatalysis offers a smooth and clean functionalization approach for drugs, with a critical assessment of current literature and highlighting expected future progress and potential applications in the field.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Chemistry, Organic

Intermolecular Trifluoromethyl-Hydrazination of Alkenes Enabled by Organic Photoredox Catalysis

Peng Wang et al.

ORGANIC LETTERS (2020)

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Review Biochemistry & Molecular Biology

Overview of recent developments of pyrazole derivatives as an anticancer agent in different cell line

Fatima Ezzahra Bennani et al.

BIOORGANIC CHEMISTRY (2020)

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Recent Advances in Photocatalytic Decarboxylative Coupling Reactions in Medicinal Chemistry

Lindsay McMurray et al.

SYNTHESIS-STUTTGART (2020)

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Article Chemistry, Organic

Rhodium-Catalyzed Room Temperature C-C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones

Bedadyuti Vedvyas Pati et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Ni-Catalyzed Denitrogenative Cross-Coupling of Benzotriazinones and Cyclopropanols: An Easy Access to Functionalized β-Aryl Ketones

Jincan Li et al.

ORGANIC LETTERS (2020)

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Copper-catalyzed stereoselective alkylhydrazination of alkynes

Jian Lei et al.

CHEMICAL COMMUNICATIONS (2020)

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4-HO-TEMPO-Catalyzed Redox Annulation of Cyclopropanols with Oxime Acetates toward Pyridine Derivatives

Jun-Long Zhan et al.

ACS CATALYSIS (2019)

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Article Chemistry, Organic

Metal-Free Cyclopropanol Ring-Opening C(sp3)-C(sp2) Cross-Couplings with Aryl Sulfoxides

Dengfeng Chen et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Asymmetric Hydrogenation of C=N Bonds Enabled by Assisted Coordination and Nonbonding Interactions

Yanhua Hu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Total syntheses via cyclopropanols

Xinpei Cai et al.

TETRAHEDRON (2019)

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Decarboxylative hydrazination of unactivated carboxylic acids by cerium photocatalysis

Veera Reddy Yatham et al.

CHEMICAL COMMUNICATIONS (2019)

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Visible-Light-Enhanced Ring Opening of Cycloalkanols Enabled by Bronsted Base-Tethered Acyloxy Radical Induced Hydrogen Atom Transfer-Electron Transfer

Rong Zhao et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Organic

Synthesis and Biological Evaluation of Piperazine Substituted 3-Aryl-5-furanyldihydropyrazole Amide Derivatives

Zewei Mao et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2018)

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Review: biologically active pyrazole derivatives

Anam Ansari et al.

NEW JOURNAL OF CHEMISTRY (2017)

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Photocatalytic C-C Bond Cleavage and Amination of Cycloalkanols by Cerium(III) Chloride Complex

Jing-Jing Guo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Organic

Photocatalytic Aminodecarboxylation of Carboxylic Acids

Simon B. Lang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

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Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations

Kunfang Jia et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Synthesis, characterization and screening for antidepressant and anticonvulsant activity of 4,5-dihydropyrazole bearing indole derivatives

Pravin O. Patil et al.

ARABIAN JOURNAL OF CHEMISTRY (2016)

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Visible light-mediated decarboxylative amination of indoline-2-carboxylic acids catalyzed by Rose Bengal

Meng-Jie Zhang et al.

RSC ADVANCES (2016)

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Direct sp3 C?H Amination of Nitrogen-Containing Benzoheterocycles Mediated by Visible-Light-Photoredox Catalysts

Yoshihiro Miyake et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

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Article Biochemistry & Molecular Biology

Synthesis and in vitro antitumor activity of new 4,5-dihydropyrazole derivatives

Cenzo Congiu et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2010)

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Article Chemistry, Medicinal

Synthesis, SAR and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles as potent cannabinoid CB1 receptor antagonists

Jos H. M. Lange et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2010)

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Article Chemistry, Medicinal

Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents

Adnan A. Bekhit et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2008)

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Article Chemistry, Medicinal

Kinesin spindle protein (KSP) inhibitors. Part 1: The discovery of 3,5-diaryl-4,5-dihydropyrazoles as potent and selective inhibitors of the mitotic kinesin KSP

CD Cox et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2005)

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Article Biochemistry & Molecular Biology

Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents

AA Bekhit et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2004)

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Review Chemistry, Multidisciplinary

The chemistry of cyclopropanols

OG Kulinkovich

CHEMICAL REVIEWS (2003)

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Cu(OAc)2-catalyzed hydrazination of cyclopropanols and late-stage transformation to 4,5-dihydropyrazoles

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