Article
Chemistry, Organic
Ilya P. Filippov, Mikhail S. Novikov, Alexander F. Khlebnikov, Nikolai V. Rostovskii
Summary: A novel strategy for the synthesis of 1-pyrrolines based on the formal [4 + 1] annulation reaction has been developed in this study. The one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization. This method shows good substrate tolerance and can be used to synthesize 1-pyrrolines containing an ester group at the C3 position.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Anastasiya Agafonova, Ilia A. Smetanin, Nikolai Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: This study presents a high-yield method for introducing a 2-pyridyl substituent in the C2 position of the three-membered ring of 2-bromo-2H-azirine-2-carboxylic acid derivatives through direct cross-coupling with 2-(trialkylstannyl)pyridines. The reaction is versatile, working well with different substituted 2-stannylpyridines and enabling the synthesis of 2-(thiazol-2-yl)-2H-azirines. DFT calculations suggest that the reaction proceeds through a sequence of S(N)2'-substitution, 1,4-stannyl shift, and [2,3]-sigmatropic shift of the pyridine ring.
Article
Chemistry, Organic
Nikita I. Efimenko, Olesya A. Tomashenko, Dar'ya V. Spiridonova, Mikhail S. Novikov, Alexander F. Khlebnikov
Summary: 2H-azirine-2-carbonyl azides undergo rearrangement into derivatives of 2-(1H-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid. Different reactions occur when interacting with primary alcohols and phenols, leading to the formation of alkyl/aryl 2-(1H-tetrazol-1-yl)acetates. Additionally, thiophenols react with 2H-azirine-2-carbonyl azides to produce S-aryl 2-(1H-tetrazol-1yl)ethanethioates. The mechanism of these nucleophile-induced rearrangements is discussed based on DFT calculations, kinetic experiments, and N-15 labeling experiments.
Article
Chemistry, Organic
Lai Chen, Jing-Qian Huo, He-Long Si, Xin-Yu Xu, Song Kou, Jianyou Mao, Jin-Lin Zhang
Summary: The study describes the first base-mediated intermolecular cyclization of arylaldehydes and terminal arylacetylenes for the synthesis of a wide range of pyrroles in a single step. The methodology utilized commercially available starting materials and tolerated a broad range of functional groups, yielding 2,3,5-triaryl-substituted-1H-pyrroles with good yields (up to 92%) under mild conditions. The possible mechanism of the reaction was also discussed.
Article
Chemistry, Organic
Shaofa Sun, Jie Huang, Cheng Yuan, Gangqiang Wang, Donghui Guo, Jian Wang
Summary: The switchable synthesis of substituted pyrimidines and 2H-imidazoles via Cu(i)-catalyzed ring expansion of 2-methoxyl-2H-azirines is described. This protocol offers a broad substrate scope and enables rapid assembly of amides, involving the selective cleavage of the C-N or C-C bond of 2H-azirines for [3 + 2] or [3 + 3] annulation reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Chinnabattigalla Sreenivasulu, Gedu Satyanarayana
Summary: We report a metal-free selective synthesis of 2-iodoenones from propargylic alcohols enabled by N-iodosuccinimide. The developed methodology also allows for the synthesis of 3,5,6-trisubstituted 2H-pyran-2-ones through a series of reactions including intermolecular Heck coupling, base-driven Michael addition, and base-mediated double bond isomerization followed by cyclo-condensation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bubul Das, Anjali Dahiya, Nikita Chakraborty, Bhisma K. Patel
Summary: Elegant synthetic strategies for chromenopyrroles (azacoumestans) have been developed by cycloaddition and lactonization reactions. The use of ethyl isocyanoacetate as a C-NH-C-C O synthon, instead of its traditional role as a C-NH-C synthon, is a key innovation. Furthermore, pentacyclic-fused pyrroles were obtained by Pd-(II) catalyzed reaction of o-iodo benzoyl chromenopyrroles.
Article
Biochemistry & Molecular Biology
Anastasiya V. Agafonova, Mikhail S. Novikov, Alexander F. Khlebnikov
Summary: Amides, anhydrides, esters, and thioesters of 2H-azirine-2-carboxylic acids were synthesized through a rapid FeCl2-catalyzed isomerization of 5-chloroisoxazoles to 2H-azirine-2-carbonyl chlorides, followed by reaction with N-, O-, or S-nucleophiles mediated by an ortho-substituted pyridine. 2-Picoline can be used as a cost-effective base when readily available chloroisoxazoles and a nucleophile are used. For high yield of acylation product, the reagent 2-(trimethylsilyl)pyridine/ethyl chloroformate is more suitable for acylation with 2H-azirine-2-carbonyl chlorides.
Article
Chemistry, Multidisciplinary
Claudia Alves, Terver J. Sase, Cristina Gadelho, Dina Murtinho, M. Elisa S. Serra, Ana L. Cardoso, Teresa M. V. D. Pinho e Melo
Summary: Several novel organocatalysts derived from beta- and gamma-lactamfused thiazolidines and L-phenylalanine-based thiazolidines were efficiently synthetized. These catalysts exhibited high enantioselectivity in the studied transformation, and the presence of the 6 beta-lactam ring was found to be essential.
Article
Chemistry, Inorganic & Nuclear
Jia Qi Tao, Hu Zhang, Wengang Bi, Xiaohui Liu, Chao Fan, Chun Sun
Summary: The study successfully developed a room temperature method for synthesizing Mn ion doped ultrathin perovskite nanoplatelets and systematically investigated the impact of Mn2+ concentration on their optical properties. Additionally, a self-purification effect of Mn ions between nanoplatelets and efficient energy transfer phenomenon were observed, which were then utilized for fabricating anti-counterfeiting film.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Gabriella Leonardi, Ada Truscello, Grazia Isa C. Righetti, Giovanni Gennaro Mondrone, Luca Mascheroni, Attilio Citterio, Roberto Sebastiano
Summary: Pyrroles are important compounds utilized in drug synthesis and material chemistry. This study presents a sustainable synthesis of N-substituted pyrrole carboxylic acid derivatives using 3-hydroxy-2-pyrones as the masked 1,4-dicarbonyl compounds that efficiently react with primary amines. The reactions can be carried out under sustainable conditions, obtaining pyrroles with high yields.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Hai Wang, Xingping Xu, Anne Neville
Summary: This study successfully prepared MoS2-x nanostructures with sulfur vacancies and demonstrated that annealing treatment can improve their electrochemical performance in supercapacitors. Sulfur vacancy defects provide additional empty states, increase carrier density, and enhance electrical conductivity, leading to an increase in specific capacitance of the material.
Article
Materials Science, Multidisciplinary
Divya Singh, Arvind Singh, Saurav K. Ojha, Animesh K. Ojha
Summary: Controlled and large-scale WSe2 nanosheets were synthesized by a simple solvothermal method and characterized by various measurements. The 2H-WSe2 electrode exhibited specific capacitance of 618.75 F/g with optimal cycling stability and retention ability. An asymmetric solid-state supercapacitor (WSe2//AC) was fabricated using WSe2 as the positive electrode and activated carbon (AC) as the negative electrode, achieving an energy density of 25.5 Wh/kg at a power density of 1111 W/kg and retaining stability of 77% at a current density of 5 A/g for 10,000 cycles. Therefore, WSe2 has potential for use as an active electrode material for sustainable energy storage devices.
Article
Chemistry, Organic
Nikolay Shcherbakov, Gleb D. Titov, Elena Chikunova, Ilya P. Filippov, Nikolai Rostovskii, Vadim Yu Kukushkin, Alexey Yu Dubovtsev
Summary: The developed modular approach to hard-to-reach non-aromatic 3H- and 2H-pyrroles is based on the integration of 2H-azirines and ynamides. The gold-catalyzed [3 + 2] cycloaddition of 2,2-disubstituted 2H-azirines and ynamides provides a high-yielding route to 5-amino-3H-pyrroles. Furthermore, the acid-promoted 1,5-shift-based isomerization of the obtained 5-amino-3H-pyrroles results in fully substituted 5-amino-2H-pyrroles, while the use of 2-substituted 2H-azirine-2-carboxylic acid leads to an aromatic 2-amino-1H-pyrrole scaffold.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jiaan Shao, Ke Shu, Shuangrong Liu, Huajian Zhu, Jiankang Zhang, Chong Zhang, Ling-Hui Zeng, Wenteng Chen
Summary: A palladium-catalyzed ring-opening reaction of 2H-azirines with hydrazones has been developed, providing an alternative route for the construction of various polysubstituted pyrazoles with a wide substrate scope. A plausible mechanism is proposed for this reaction, enriching the chemical conversion of 2H-azirines.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)