Article
Chemistry, Organic
Jianli Zheng, Yingqian Xu, Shaorui Song, Ling Huang, Dongdong Cao, Aiguo Zhong, Jianguo Yang, Dingben Chen
Summary: The photoredox-catalyzed 1,6-difluoromethylation of 3-methyl-4-nitro-5-styrylisoxazole with HCF2SO2Na has been developed, yielding structurally diverse difluoromethylated products. The di-, tri-, and monofluoromethylation were compared, showing the highest yield for difluoromethylation. DFT calculations revealed the nucleophilicity of CF2H radical and the lowest transition state activation energy in the difluoromethylation reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Anastasiia Klochkova, Andrey Bubyrev, Dmitry Dar'in, Olga Bakulina, Mikhail Krasavin, Viktor Sokolov
Summary: A novel tandem approach has been developed for the synthesis of various isothiazolidine 1,1-dioxides. The method involves N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition, leading to high yields and trans-diastereoselectivity. The reactivity dependency on the electronic properties of substrates has been investigated.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Abhisek Midya, Laxman Devidas Khalse, Prasanta Ghorai
Summary: In this study, an amine-catalyzed reductive aldol-condensation followed by an intramolecular reductive Michael-addition cascade was demonstrated, using Hantzsch ester as a hydride source to a keto-bis-enone, leading to the synthesis of enantio- and diastereoselective benzannulated diquinanes with three consecutive stereocenters, including an all-carbon quaternary formyl stereocenter. Interestingly, changing the tether from an aliphatic to an aromatic moiety resulted in a change in reactivity, where an asymmetric aldol reaction, followed by an iminium/enamine isomerization and diastereoselective Michael addition reaction, resulted in the formation of a bis-benzannulated diquinane with vicinal congested quaternary chiral centers.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Surajit Duari, Subrata Biswas, Arnab Roy, Srabani Maity, Abhishek Kumar Mishra, Aguinaldo R. Souza, Asma M. Elsharif, Nelson H. Morgon, Srijit Biswas
Summary: In this study, a catalytic synthetic strategy was developed to access various N-functionalized heterocyclic derivatives. The reaction involves the direct nucleophilic substitution of alcohols followed by X to N alkyl group migration. Methyl trifluoromethanesulfonate was found to be an efficient catalyst for this reaction. The mechanism was elucidated through experiments and DFT calculations.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Javier Garcia-Dominguez, Marina Carranza, Edijs Jansons, Ana T. Carmona, Inmaculada Robina, Antonio J. Moreno-Vargas
Summary: This paper presents the use of 7-oxa/azanorbornadienes as synthetic intermediates for the preparation of 3/4-substituted furans/pyrroles. The method involves the inverse electron demand Diels-Alder (iEDDA) cycloaddition and retro-Diels-Alder (rDA) reactions, resulting in the synthesis of beta-substituted furans/pyrroles. The study explores the application of this method in the preparation of 29 heterocycles and proposes a one-pot procedure.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shinichiro Fuse, Sena Kanda, Hisashi Masui
Summary: Valuable indole derivatives were synthesized via the sequential 1,2-addition/nucleophilic substitution of indolyl-3-carbaldehydes. Microflow technology was used to suppress undesired reactions caused by unstable intermediates, leading to higher yields and reproducibility. The study provides a rapid and efficient method for the synthesis of structurally diverse indole derivatives.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Stefano Barranco, Federico Cuccu, Dayi Liu, Sylvie Robin, Regis Guillot, Francesco Secci, Valerie Brenner, Michel Mons, Pierluigi Caboni, David J. Aitken, Angelo Frongia
Summary: A new method for the stereoselective one-pot double derivatization of cyclobutene-1-carboxylic acid has been developed. This method involves a mild organic base catalyzed amidation/aza-Michael addition of benzo[d]oxazol-2(3H)-ones, leading to the formation of novel beta-N-heterocyclic cyclobutane carboximide derivatives with a trans geometry. The carboximide moiety can react smoothly with nucleophiles, providing access to diverse derivatives of trans-beta-N-heterocyclic cyclobutanecarboxylic acid, including peptidomimetic structures.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dmytro I. Sierov, Illia V. Dzhulai, Kateryna I. Siryk, Kostiantyn V. Shvydenko, Tetiana I. Shvydenko, Kostiantyn Nazarenko, Aleksandr Kostyuk, Oleksandr S. Liashuk, Oleksandr O. Grygorenko
Summary: A systematic study on the SnAr reaction of halogenated fluoropyridines with (hetero)aliphatic nitrile anions was conducted, leading to the synthesis of functionalized pyridines bearing a (cyclo)alkyl or saturated heterocyclic substituent. The method demonstrated high chemo- and regioselectivity, as well as excellent scalability, and was applicable to various (hetero)aliphatic nitriles and isomeric halogenated 2- and 4-fluoropyridines. The synthesized products showed utility in additional functional group transformations, providing valuable pyridine-containing building blocks.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tetsuya Sengoku, Haruka Iwama, Takuma Shimotori, Keisuke Fujimoto, Toshiyasu Inuzuka, Koki Matsune, Hidemi Yoda
Summary: In this study, a heavy-metal-free reductive coupling of arylacetylenes with benzothiazole sulfones is proposed. The reactions of alkyl or benzylic benzothiazole sulfones with arylacetylenes are successfully carried out in the presence of Hantzsch esters and K2CO3 under visible-light irradiation, resulting in moderate to good yields of 1,2-disubstituted alkenes, with the Z-isomer as the major product. The utility of this protocol is expanded to a-deuterative coupling, providing the corresponding alkenes with high deuterium incorporation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tetsuya Sengoku, Haruka Iwama, Takuma Shimotori, Keisuke Fujimoto, Toshiyasu Inuzuka, Koki Matsune, Hidemi Yoda
Summary: In this study, a heavy-metal-free reductive coupling reaction of arylacetylenes with benzothiazole sulfones is proposed. The reaction of alkyl or benzylic benzothiazole sulfones with arylacetylenes is successfully achieved under visible-light irradiation in the presence of Hantzsch esters and K2CO3, giving moderate to good yields of 1,2-disubstituted alkenes with Z-isomer as the major product. The utility of this method is further expanded to a-deuteration coupling reaction using a deuterated Hantzsch ester, leading to the corresponding alkenes with high deuterium incorporation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Pham Duy Quang Dao, Chan Sik Cho
Summary: A class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]quinazolines and -pyrimidines, were successfully synthesized in good yields using a microwave-assisted coupling and cyclization process with 2-(2-Bromoaryl)- and 2-(2-bromovinyl)benzimidazoles as building blocks. The reaction is believed to proceed through an initial C(sp(2))-N coupling followed by a nucleophilic aromatic substitution (SNAr) and cyclization, resulting in the extrusion of alcohols.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhan-Cai Li, Yu Zhang, Bing-Xia Yan, Xiao-Ning Wang, De-Hua Zhai, Qiang Li, Hong-Xing Zheng, Chang-Qiu Zhao
Summary: Biphenyl derived secondary phosphine oxides with 2'-hydroxyl were synthesized and converted to hydroxymethyl phosphine oxides. Chlorination and cyclization led to the formation of a series of P,O-heterocycles. Under LDA treatment, rearrangement occurred to stereoselectively produce hydroxyl substituted cyclic phosphines. The rearrangement was proposed to involve intra-molecular aromatic substitution reactions, resulting in the conversion of P-stereogenic secondary phosphine oxide to a P,C,axial-stereogenic P-cycle.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Andreia M. P. W. Da Silva, Mateus Mittersteiner, Fabio M. Da Silva, Fernanda D'Avila, Pablo A. Nogara, Karise F. Nogara, Joao B. T. Rocha, Helio G. Bonacorso, Marcos A. P. Martins, Nilo Zanatta
Summary: A chemoselective approach was used to synthesize compounds with 4-(bromo/chloro)methyl-2-methylsulfanyl-6-trihalomethyl pyrimidines, which were further substituted with aminoalcohols. The resulting choline derivatives showed potential as AChE and BChE inhibitors, with the trichloromethyl pyrimidines exhibiting the highest activity. Docking studies and ADMET properties were also reported.
Review
Chemistry, Applied
Anna Gulevskaya, Daria Tonkoglazova
Summary: Helicenes are polycyclic aromatic molecules with unique structures and properties. They have been widely applied in material science, nanoscience, and other fields. However, synthesizing helicenes remains a challenge, and alkyne cyclizations show great potential as a method. This review focuses on the development and applications of alkyne-based syntheses of carbo- and heterohelicenes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Lusine V. Karapetyan, Gayane G. Tokmajyan
Summary: The catalyst-free and eco-friendly synthesis of potentially bioactive compounds comprising iminodihydrofuran and thiazolidinone rings has been developed using two strategies from iminodihydrofuran thiosemicarbazones. The methodologies are simple, efficient, inexpensive, and yield good to excellent yields of the polyheteroconjugated products with operational simplicity.
Article
Chemistry, Medicinal
Dhrubajyoti Datta, Swagata Dasgupta, Tanmaya Pathak
Article
Chemistry, Multidisciplinary
Chinmoy Manna, Tanmaya Pathak
Article
Biochemistry & Molecular Biology
Anirban Kayet, Dhrubajyoti Datta, Ashrukana Das, Swagata Dasgupta, Tanmaya Pathak
BIOORGANIC & MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Organic
Anirban Kayet, Tanmaya Pathak
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Organic
Jayanta Das, Santu Dey, Tanmaya Pathak
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Ashrukana Das, Atanu Bhaumik, Tanmaya Pathak
CARBOHYDRATE RESEARCH
(2020)
Article
Chemistry, Physical
Mini Loya, Samiul Islam Hazarika, Pallab Pahari, Ananta Kumar Atta
Summary: Novel triazole-appended quinoline and naphthyl-based fluorescent sensors 1 and 2 were developed from D-glucose. Sensor 1 exhibited excimer emission in solvent, while model compound 2 did not. The detection ability of sensor 1 for Cu2+ and Ni2+ ions in aqueous methanolic solution was confirmed, with a detection limit of 1.01μM for Cu2+ and 1.46μM for Ni2+.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Biochemical Research Methods
Mini Loya, Bholanath Dolai, Ananta Kumar Atta
Summary: The sensing properties of naphthaldimine-glucofuranose conjugates 1 and 2 towards metal ions were investigated using various spectroscopic methods. The results showed that compound 1 formed 1:1 coordination complexes with Fe2+ and Cu2+ ions, resulting in color changes. The formation of 1-Fe2+ and 1-Cu2+ complexes was analyzed using different experimental techniques.
JOURNAL OF FLUORESCENCE
(2022)
Article
Chemistry, Organic
Kumares Sarkar, Tanmaya Pathak
Summary: Terminal vinyl sulfones derived from styrene epoxide and monomesylated glycerol were reacted with benzylazide in a metal-free condition to regioselectively obtain 1,4-disubstituted 1,2,3-triazoles via Eliminative Azide-Olefinic Cycloaddition (EAOC) reactions. The use of a N, N-dimethyl ethanolammonium formate-water mixture significantly reduced reaction time and increased yield. Furthermore, the reaction of azido sugars with terminal vinyl sulfone modified carbohydrates yielded 1,4-disubstituted 1,2,3-triazole linked bissacharides, providing a potential route for direct connection of carbon units to sugar bodies.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Ananta Kumar Atta, Samiul Islam Hazarika, Mini Loya, Santanab Giri
Summary: The sugar-modified simple fluorometric sensors 1 and 2 for detection of Au3+ in the aqueous acetonitrile have remarkable selectivity and excellent sensitivity.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ashrukana Das, Swagata Dasgupta, Tanmaya Pathak
Summary: This study demonstrates the design and screening of a new class of benzene-based triazolylated semicircular hybrid molecules as ribonuclease A inhibitors. The addition of a carboxylic acid group at the C1-position of the 1,3,5-trisubstituted benzene ring and the reduction of arm lengths of 3,5-substituents enhance the inhibitory properties significantly.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Pampa Mondal, Swagata Dasgupta, Tanmaya Pathak
Summary: Molecular docking studies showed that N-1,4-disubstituted-1,2,3-triazole tethered carboxymethylated thymidine and uridine can potentially bind to the P1, B1, and P2 subsites of ribonuclease A. The findings from this study, combined with previous experimental observations, were used to guide the design of a range of 1,4-disubstituted 1, 2, 3-triazole tethered carboxymethylated pyrimidine nucleosides.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Physical
Mini Loya, Suprava Ghosh, Ananta Kumar Atta
Summary: Organic molecular probes have been developed for simultaneous detection of Cu2+ and Ni2+ ions, based on their binding chemistry and changes in absorbance/fluorescence. This is the first report on the dual detection of Cu2+ and Ni2+ ions.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Dhrubajyoti Datta, Swagata Dasgupta, Tanmaya Pathak
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Ashrukana Das, Swagata Dasgupta, Tanmaya Pathak
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)