Article
Chemistry, Organic
Eliott Le Du, Julien Borrel, Jerome Waser
Summary: In this study, a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents was reported. Nonsymmetrical ynehydrazides could be obtained in high yields using azaglycine derivatives as nucleophiles. The reaction is compatible with various functional groups naturally occurring on amino acid side chains and allows the transfer of different substituents. The obtained products can be further functionalized.
Review
Chemistry, Organic
Chukuka Achuenu, Sebastien Carret, Jean-Francois Poisson, Florian Berthiol
Summary: Chiral alpha-tertiary amines, a motif found in various natural products, drugs, and drug candidates, can be synthesized by adding organometallic reagents or other nucleophiles to chiral N-sulfinylketimines. This synthetic strategy has wide applications in the synthesis of biologically active compounds.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Pargat Singh, Mahendra Nath
Summary: A catalyst-free synthetic approach to beta-thiazole-fused 5,10,15,20-tetraarylporphyrins via a cascade reaction of nickel(II) or copper(II) 2-amido-3-bromo-5,10,15,20-tetraarylporphyrins and Lawesson's reagent is described in this study. The novel porphyrins showed significant bathochromic shift in electronic absorption and emission spectra compared to their precursors, meso-tetraarylporphyrins, as revealed by preliminary photophysical studies.
Article
Chemistry, Organic
Eri Ogino, Ayu Nakamura, Satoru Kuwano, Takayoshi Arai
Summary: AMB4 is an efficient organocatalyst for the asymmetric epoxidation of various alkylidenemalononitriles, leading to the formation of chiral dihydroquinoxalinyl spirooxindoles from isatilidenemalononitriles.
Article
Chemistry, Multidisciplinary
Jia-Wang Wang, Zhen Li, Deguang Liu, Jun-Yang Zhang, Xi Lu, Yao Fu
Summary: Site- and enantio-selective alkyl-alkyl bond formation via nickel-catalyzed remote asymmetric hydro-alkylation of alkenyl ethers is reported. This reaction demonstrates synchronous alkene isomerization and enantioselective C(sp(3))-C(sp(3)) bond formation. The reaction has broad substrate scope, good functional group tolerance, excellent regioselectivity (>20:1 regioisomeric ratio), and high enantioselectivity (up to 95% enantiomeric excess).
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Xuelin Yue, Yijie Gao, Junwei Huang, Yadong Feng, Xiuling Cui
Summary: An efficient method for synthesizing N substituted indenoisoquinolinones has been developed through rhodium(III)-catalyzed C-H bond activation/subsequent [4 + 2] cyclization. The reaction starts from readily available 2-phenyloxazolines and 2-diazo-1,3-indandiones. This protocol offers excellent atom- and step-economy, providing a novel strategy for the synthesis of N-substituted indenoisoquinolinones and enabling the study of their biological activities.
Article
Chemistry, Organic
Xuelin Yue, Yijie Gao, Junwei Huang, Yadong Feng, Xiuling Cui
Summary: An efficient method for the synthesis of N substituted indenoisoquinolinones has been developed via rhodium(III)-catalyzed C- H bond activation and subsequent [4 + 2] cyclization. The reaction uses 2-phenyloxazolines and 2-diazo-1,3-indandiones as starting materials and proceeds through C-H functionalization, intramolecular annulation, elimination, and ring opening in one pot under mild conditions, yielding a series of indeno[1,2-c]isoquinolinones with up to 93% yield. This method demonstrates excellent atom-and step-economy and provides a novel strategy for the synthesis of N substituted indenoisoquinolinones and their study of biological activities.
Article
Chemistry, Multidisciplinary
Ronghua Lu, Tilong Yang, Xin Chen, Wenzheng Fan, Pinhong Chen, Zhenyang Lin, Guosheng Liu
Summary: The first enantioselective copper-catalyzed cyanation of propargylic C-H bonds via radical relay has been established using novel Box(OTMS) ligands, providing an efficient tool for constructing structurally diverse chiral allenyl nitriles with high yields and excellent enantioselectivities. The reaction features high functional group tolerance and mild conditions, and the chiral allene products can be easily converted to other chiral compounds via axis-to-center chirality transfer.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Yishou Wang, Xiaohan Zhu, Deng Pan, Jierui Jing, Fen Wang, Ruijie Mi, Genping Huang, Xingwei Li
Summary: Here, the authors report the construction of diverse classes of diaxially chiral biaryls containing N-N and C-N/C-C diaxes in excellent stereo- and diastereoselectivity. The N-N chiral axis in the products allows for solvent-driven diastereodivergence, as demonstrated in the coupling of benzamides and sterically hindered alkynes. The mechanism of diastereodivergence is elucidated through computational studies, revealing the role of hexafluoroisopropanol (HFIP) as a solvent and ligand.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Tobias Brandhofer, Martin Stinglhamer, Volker Derdau, Maria Mendez, Christoph Poeverlein, Olga Garcia Mancheno
Summary: A visible light-mediated photocatalyzed C-C-bond forming method has been developed for the benzylic C-H functionalization of phenolether containing synthetic building blocks based on a radical-cation/deprotonation strategy. This method enables the mild, selective generation of benzyl radicals in phenolic complex molecules and drug-like compounds, offering new opportunities in synthetic and medicinal chemistry.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Pradyota Kumar Behera, Papita Behera, Amlan Swain, Santosh Kumar Sahu, Ajeena Sahoo, Laxmidhar Rout
Summary: We have developed a simple and direct method for the synthesis of diaryl ether using an oxygen bridged bimetallic CuMoO4 nanocatalyst under mild reaction conditions. The catalyst exhibited tolerance towards a wide range of substrates with various functional groups. It is efficient and recyclable. This methodology allows easy access to nitrofen derivatives (herbicides) from unactivated 2,4-dichlorophenol, which are important for agriculture and pharmaceuticals.
NEW JOURNAL OF CHEMISTRY
(2024)
Article
Biochemistry & Molecular Biology
Alice Benzi, Lara Bianchi, Gianluca Giorgi, Massimo Maccagno, Giovanni Petrillo, Domenico Spinelli, Cinzia Tavani
Summary: Nitrostilbenes with different aryl substituents can be obtained from the initial ring-opening of 3-nitrobenzo[b]thiophene with amines. These versatile compounds exhibit diverse reactivity and can undergo electrocyclization to form novel naphthodihydrofurans. Aromatization and electrocyclization of these compounds further lead to valuable polycondensed O-heterocycles.
Article
Chemistry, Inorganic & Nuclear
Luis Tarifa, Ana M. Geer, Laura Asensio, Jose A. Lopez, Miguel A. Ciriano, Cristina Tejel
Summary: The ability of a heteroditopic ligand to create separate compartments for metals in different oxidation states has been developed and studied.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mahesh Kumar, Ramesh Kumar Vishwakarma, Preeti, Krishna Nand Singh
Summary: An efficient method for the C(sp(3))-H functionalization of alkyl arylacetates using CS2 and amines by eosin Y/I-2 dual catalysis has been developed, leading to the formation of S-benzyl dithiocarbamate acetates.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Xianda Wu, Yuqing Li, Minghong Chen, Fu-Sheng He, Jie Wu
Summary: A novel and efficient method for the synthesis of sulfilimines has been developed using diaryliodonium salts for the S-arylation of sulfenamides. The reaction proceeds smoothly under transition-metal-free and air conditions, resulting in good to excellent yields of sulfilimines via selective S-C bond formation. This scalable protocol exhibits a broad substrate scope, good functional group tolerance, and excellent chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Amit Kumar, Gautam Panda
Summary: In this study, a novel reaction method utilizing Magnesium chloride (MgCl2) catalysis was successfully developed for the highly C3-selective ring-opening reaction of 2,3-epoxy alcohols with N-nucleophiles and sodium azide. The reaction proceeded under mild conditions and showed high yields of the desired 3-amino-1,2 diols and 3-azido-1,2 diols, demonstrating practicality and broad functional group tolerance.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Physical
Deblina Roy, Kasim Ali, Gautam Panda
Summary: The study reveals a method using Wilkinson catalyst for hydroacylation simplifies the synthesis of bedaquiline analogs with reduction of steps. Direct installation of three crucial aryl rings in the reaction leads to a series of bedaquiline analogs.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Deblina Roy, Grace Kaul, Abdul Akhir, Ashok Kumar Sharma, Satyen Saha, Sidharth Chopra, Gautam Panda
Summary: A library of diarylmethyl amines targeting ESKAPE bacterial pathogens was synthesized, and compounds with potent antibacterial activity against Gram-positive bacteria were identified. The presence of lipophilic and nitrogenous components was found to be important for antibacterial activity.
Article
Chemistry, Organic
Amit Kumar, Gaurav Sharma, Sanjeev K. Shukla, Gautam Panda
Summary: A tandem reaction involving semipinacol rearrangement and aldehyde arylation or alkylation has been discovered. This reaction allows for the formation of functionalized 1,3-diols bearing three consecutive tertiary stereocenters from various trisubstituted 2,3-epoxy alcohols and Grignard reagents. The resulting 1,3-diols are confirmed to exist in the anti configuration.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Amit Kumar, Neetu Kumari, Sandeep Bhattacherjee, Umamageswaran Venugopal, Shahid Parwez, Mohammad Imran Siddiqi, Manju Y. Krishnan, Gautam Panda
Summary: Novel chemical compounds were discovered to inhibit the bc1 complex mutant of Mycobacterium tuberculosis, with two molecules showing MICs of 8 and 16 mu M, compared to MICs of 128 and 256 mu M against the wild type. These compounds were bactericidal to wild type bacteria under hypoxic conditions at concentrations much lower than their MICs, and showed synergy with an inhibitor of the bc1 complex in inhibiting bacterial growth.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kasim Ali, Gautam Panda
Summary: An efficient transition-metal-free multicomponent approach to the regioselective synthesis of highly substituted N-alkylpyrazoles through 1,6-addition of pyrazole (in situ generated from alpha,beta-unsaturated aldehyde and hydrazide) to para-Quinone Methides has been developed. The N-alkylpyrazole containing triarylmethanes having several heteroaryl rings (quinoline, pyridine, thiophene) at the central methine carbon atom was developed. This chemical process may be used for large-scale synthesis and provides a novel way to produce triarylmethanes with diverse functional groups.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Review
Chemistry, Medicinal
Indranil Chatterjee, Kasim Ali, Gautam Panda
Summary: This review critically analyzes the synthetic strategies and anticancer activities of benzoxazines and benzoxazepines compounds reported from 2010 onwards. The structure-activity relationship of the benzoxazine and benzoxazepine scaffolds containing bioactive compounds is also studied, focusing on how structural modification affects their anticancer activity.
Review
Chemistry, Multidisciplinary
Arpita Banerjee, Indranil Chatterjee, Gautam Panda
Summary: This article discusses the significance of tyrosine as a chiral pool in the synthesis of alkaloids, and compares synthetic steps, overall yield, and other factors between tyrosine-based and non-tyrosine-based routes.
Article
Chemistry, Multidisciplinary
Saroj Maji, Souvik Barman, Gautam Panda
Summary: In this study, a novel synthetic route towards nintedanib was developed using a stereoselective intramolecular cyclization strategy to convert beta-keto amide into a 3-acyloxindole derivative, an important scaffold for nintedanib synthesis. The condensation of the oxindole scaffold with a synthesized amine derivative led to the successful synthesis of nintedanib.
Article
Chemistry, Organic
Indranil Chatterjee, Gautam Panda
Summary: This paper describes a palladium-catalyzed regioselective reaction of propargylic carbonate with thiophenols and benzene selenol. The addition of thiols to propargylic carbonates provides an atom-economic and effective process. The reaction proceeds through hydrothiolation to produce mono(arylthiol) alkenes and hydrothiolation followed by Tsuji-Trost type substitution to form bis(arylthiol) alkenes by controlling the equivalence of thiophenols. This coupling reaction exhibits good tolerance towards functional groups and leads to the formation of highly functionalized alkenylation products via the formation of new C-S and C-Se bonds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Indranil Chatterjee, Gautam Panda
Summary: A simple and efficient metal-free approach was developed for synthesizing 4-thio-substituted chroman and diarylmethyl thioethers, providing good yields and tolerance for labile functional groups. This method is applicable to large-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Gurudayal Prajapati, Ravi Sankar Ampapathi, Gautam Panda
Summary: The reductive coupling between allylic sulfonylhydrazones and aryl boronic acids can efficiently generate 1,3-diarylpropene systems under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Arpita Banerjee, Gautam Panda
Summary: In this study, a base mediated, transition metal-free intermolecular epoxide ring opening reaction followed by intramolecular aromatic nucleophilic substitution (SNAr) was developed to synthesize separable diastereomers of selected benzo[b][1,4,5]oxathiazepine 1-oxides. This strategy allows the formation of both C-N and C-O bonds simultaneously in a single step. The method has a wide substrate scope, uses simple reaction conditions, and is applicable for synthesizing bioactive molecules with similar skeletons as benzoxathiazepine 1-oxides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Kasim Ali, Prajjval Mishra, Awnish Kumar, Damodara N. Reddy, Sushobhan Chowdhury, Gautam Panda
Summary: In this article, the synthesis, structure-reactivity relationships, and synthetic applications of quinone methides are discussed. The formation of intermediates during bioactivation and potential chemical manifestations leading to toxicity in biological systems are also covered.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Deblina Roy, Abhineet Verma, Arpita Banerjee, Satyen Saha, Gautam Panda
NEW JOURNAL OF CHEMISTRY
(2020)