Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski
Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Kai-Kai Wang, Yan-Li Li, Rong-Xiang Chen, Ai-Li Sun, Zhan-Yong Wang, Ying-Chao Zhao, Ming-Yue Wang, Shi Sheng
Summary: The additive-free 1,3-dipolar cycloaddition reaction enables diversity-oriented synthesis of novel and structurally complex derivatives in high yields and excellent diastereoselectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Guipeng Feng, Guoyang Ma, Wenyan Chen, Shaohong Xu, Kaikai Wang, Shaoyan Wang
Summary: The [3 + 2] 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved, resulting in a range of tetrahydroisoquinoline derivatives with good diastereoselectivities and enantioselectivities. The absolute configuration of the product was determined using quantum electronic circular dichroism calculation and ECD spectrum method.
Article
Chemistry, Multidisciplinary
Houda Gazzeh, Fadwa Rouatbi, Sami Chniti, Moheddine Askri, Michael Knorr, Carsten Strohmann, Christopher Golz, Al Mokhtar Lamsabhi
Summary: The mechanism of a three-component one-pot cycloaddition reaction was studied using both theoretical and experimental methods. The reactivity difference between the unsymmetrical exocyclic dienones was analyzed to explain the observed regio- and stereoselectivity, and the results were confirmed by calculations. The reaction proceeded under kinetic control and showed chemoselectivity, producing two highly diastereomerically enriched compounds. The intermolecular hydrogen bonding and optical properties of the products were also investigated.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mohammed F. F. Radwan, Elghareeb E. E. Elboray, Hemat M. M. Dardeer, Yusuke Kobayashi, Takumi Furuta, Shohei Hamada, Toshifumi Dohi, Moustafa F. F. Aly
Summary: 1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Metal-free AcOH-activated 1,3-dipolar cycloaddition protocol was developed to synthesize uncommon pyrrolidine cycloadducts with excellent diastereoselectivity. The reaction mechanism and the key role of AcOH were supported by experimental, theoretical and spectroscopic studies.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Ruo-Qing Wang, Chong Shen, Xiang Cheng, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, copper-catalyzed asymmetric propargylic substitution was successfully achieved using salicylaldehyde-derived imine esters and propargylic carbonates, resulting in a wide range of chiral amino acid derivatives containing propargylic groups. The ortho-hydroxy group of the salicylaldehyde-derived imine esters played a crucial role in increasing reactivity and stabilizing the azomethine ylide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Guangjun Bao, Peng Wang, Guofeng Li, Changjun Yu, Yiping Li, Yuyang Liu, Zeyuan He, Tiantian Zhao, Jing Rao, Junqiu Xie, Liang Hong, Wangsheng Sun, Rui Wang
Summary: A new method for 1,3-dipolar cycloaddition reactions between different types of amino acids to generate various quaternary amino acids was disclosed in this study. This method can also be applied within peptide chains, providing a new approach for late-stage peptide modification and drug conjugation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Qiumi Wang, Sicheng Li, Guosheng Yang, Xinyu Zou, Xi Yin, Juhua Feng, Huabao Chen, Chunping Yang, Li Zhang, Cuifen Lu, Guizhou Yue
Summary: The allylation of N-unsubstituted isatin N,N'-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature resulted in the rapid formation of N-allylated and N, beta-diallylated isatin N,N'-cyclic azomethine imine 1,3-dipoles in moderate to high yields. This reaction offers mild reaction conditions, practical operability, and short reaction times in most cases. Furthermore, the alkylated products can be transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through [3+2] or [3+3]-cycloaddition reactions with maleimides or Knoevenagel adducts.
Article
Chemistry, Organic
Asmaa Belabbes, Veronica Selva, Francisco Foubelo, M. De Gracia Retamosa, Jose M. Sansano
Summary: The synthesis of complex spiro{pyrrolidine-3,1'-pyrrolo[3,4-c]pyrrole} skeleton under mild conditions is presented, with the order of addition of a primary amine and two equivalents of corresponding maleimide being crucial for high yields. The mechanism was studied by simple tests, revealing the Michael type addition of the amine onto the maleimide as a key step. Interesting scaffold hybrids were prepared through sequential addition of two different maleimides, and a more intriguing architecture was obtained through a metathesis reaction between allylic residues in the molecule precursor.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Shahnaz Rahimi, Mehdi Ghandi, Maryam Fallahnezhad, Alireza Abbasi
Summary: A novel chromeno[3,4-c]spiropyrrolidine-indenoquinoxalines have been synthesized via a one-pot, four-component reaction by 1,3-dipolar cycloaddition of 3-acetyl-coumarins with azomethine ylides followed by deacetylation and protonation (deuteration). The products were obtained in moderate to high yields and their structures were confirmed by H-1 NMR, C-13 NMR, FT-IR, and MS spectroscopy.
MOLECULAR DIVERSITY
(2023)
Article
Biochemistry & Molecular Biology
Guosheng Yang, Sicheng Li, Qiumi Wang, Huabao Chen, Chunping Yang, Zhongqiong Yin, Xu Song, Li Zhang, Cuifen Lu, Guizhou Yue
Summary: The synthesis of dicyclic spiropyridazine oxoindole derivatives by [3+3]-cycloaddition reaction of N-unsubstituted isatin N,N'-cyclic azomethine imine 1,3-dipoles was successfully achieved. The products, having two consecutive stereocenters including spiroquaternary stereocenters in one ring structure, were obtained in moderate to excellent yields (20-93%) and low to moderate diastereoselectivities (1:9-10:1 dr). The synthesized compounds were thoroughly characterized using various spectroscopic techniques.
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Chemistry, Organic
Mamta Gill, Arko Das, Vinod K. Singh
Summary: An enantioselective (3+2) cycloaddition reaction has been reported for the synthesis of chiral polysubstituted pyrrolidines. The reaction displays opposite regioselectivity with excellent enantioselectivities and yields. Interestingly, changing the alpha-substituents of the iminoesters results in the formation of normal (3+2) cycloaddition products with excellent enantioselectivities as well.
Article
Chemistry, Organic
Kelvin J. Y. Wu, Amy E. Benedetto, Andrew G. Myers
Summary: The regioselectivity of a [3+2] dipolar cycloaddition reaction between a stabilized azomethine ylide and an electron-deficient dipolarophile is contrary to a previous report in this journal.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shohei Furuya, Kenji Muroi, Kazuya Kanemoto, Shin-ichi Fukuzawa
Summary: The stereodivergent asymmetric synthesis of 2,5-trans/cis pyrrolidines by 1,3-dipolar cycloaddition using two different types of activated alkenes is described. The reaction using ylidene-isoxazolones as dipolarophiles produced 2,5-trans pyrrolidines, while the reaction using acyclic enones as activated alkenes afforded 2,5-cis substituted pyrrolidines.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Sudipta K. Kundu, Anirban Kayet, Ramlal Baidya, Lanka Satyanarayana, Dilip K. Maiti
Article
Chemistry, Multidisciplinary
Manas Mahapatra, Arnab Dutta, Joy Sankar Deb Roy, Mousumi Deb, Ujjal Das, Snehasis Banerjee, Sanjit Dey, Pijush Chattopadhyay, Dilip K. Maiti, Nayan Ranjan Singha
Article
Chemistry, Organic
Rajesh Nandi, Prakash K. Mandal, Anirban Kayet, Tamalika Bhattachariya, Sukla Ghosh, Dilip K. Maiti
Article
Nanoscience & Nanotechnology
Tanmoy Ghosh, Somrita Mondal, Rituparna Maiti, Sk Masum Nawaz, Narendra N. Ghosh, Enakshi Dinda, Amrita Biswas, Suman Kumar Maity, Abhijit Mallik, Dilip K. Maiti
Summary: Organic fluorescent semiconducting nanomaterials based on pyrazaacene derivatives were efficiently synthesized and displayed high solubility, fluorescence, and photostability. The compounds showed efficient solvent-dependent fluorescence in the visible region and were associated through complementary interactions to afford nanomaterials with a low band gap. Remarkably, the fabricated stacked nanomaterial system exhibited resistive switching behavior, leading to the development of an efficient write-once-read-many-times memory device.
Review
Chemistry, Organic
Krishnanka Shekhar Gayen, Titiksha Das, Nirbhik Chatterjee
Summary: Molecules with three primary amine groups are common in synthetic chemistry and are excellent precursors for designing and synthesizing various cage molecules. These compounds have made significant contributions to supramolecular chemistry, synthetic methodology, and material science.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Debabrata Barman, Tanmoy Ghosh, Krishanu Show, Sudipto Debnath, Tapas Ghosh, Dilip K. Maiti
Summary: The N-heterocyclic carbene-catalyzed tandem Stetter-aldol reactions of phthalaldehyde and alpha,beta-unsaturated ketimines yielded functionalized naphthalen-1(2H)-one derivatives as [4+2] annulation products, while the reactions of aldimines resulted in the formation of isoquinoline derivatives instead of the expected indanone derivatives as [4+1] annulation products, showcasing a novel synthetic strategy.
Article
Chemistry, Analytical
Arnab Dutta, Manas Mahapatra, Madhushree Mitra, Akash Banerjee, Narendra Nath Ghosh, Pijush Kanti Chattopadhyay, Dilip K. Maiti, Nayan Ranjan Singha
Summary: By synthesizing two non-conventional fluorogens, sensitive detection and exclusion of Cu(II) and Fe(III) from hazardous effluents were achieved, as well as their application in cell imaging. Through various analysis methods, the structures and properties of the fluorogens were thoroughly investigated.
SENSORS AND ACTUATORS B-CHEMICAL
(2021)
Article
Chemistry, Physical
Habiba Sultana, Manas Barai, Manas Kumar Mandal, Emili Manna, Dilip Kumar Maiti, Dibakar Dhara, Amiya Kumar Panda
Summary: The interfacial and aggregation behavior of sodium cholate and sodium deoxycholate in aqueous ionic liquid were studied. It was found that both IL and NaBF4 were able to reduce the critical micelle concentration of bile salts, with IL inducing the formation of larger aggregates by bile salts. Such systems are considered to have potential applications where the dual benefit of both a surfactant and an IL are warranted.
JOURNAL OF DISPERSION SCIENCE AND TECHNOLOGY
(2022)
Article
Environmental Sciences
Himarati Mondal, Mrinmoy Karmakar, Narendra Nath Ghosh, Dilip K. Maiti, Pijush Kanti Chattopadhyay, Nayan Ranjan Singha
Summary: In this study, an optimum sodium alginate-grafted hydrogel was selected among twelve synthesized hydrogels for adsorption of arsenic and vanadium. The grafted hydrogel showed improved swelling, crosslink density, and adsorption capacity, making it suitable for efficient removal of As(III) and V(V).
JOURNAL OF ENVIRONMENTAL MANAGEMENT
(2021)
Article
Physics, Multidisciplinary
Rituparna Maiti, Narendra Nath Ghosh, Abdul Ashik Khan, Nabajyoti Baildya, Dilip K. Maiti
Summary: Density functional theory calculations have revealed the influence of alkali metal doping on the activation of CO2 in nano-hollow cages A12X12, with potassium-doped endohedral nanocages showing the lowest energy barrier for CO2 activation. These findings provide new insights for the design of potential nanocage catalysts for CO2 reduction.
Article
Integrative & Complementary Medicine
Arijit Ghosh, Tanaya Roychowdhury, Rajesh Nandi, Rituparna Maiti, Narendra N. Ghosh, Sabir A. Molla, Soma Mukhopadhyay, Chandraday Prodhan, Keya Chaudhury, Priyabrata Das, Nirmal K. Sarkar, Samit Chattopadhyay, Rittwika Bhattacharya, Chinmoy K. Bose, Dilip K. Maiti
Summary: Moringa oleifera Lam. root extract showed cytotoxic activity, induced apoptosis, and reduced FSHR and c-Myc expression in epithelial ovarian cancer cells. The active compound identified as a naturally hydrated-trifattyglyceride has a folded amphipathic structure for easy transportation in biological systems.
JOURNAL OF TRADITIONAL AND COMPLEMENTARY MEDICINE
(2021)
Article
Chemistry, Organic
Rajjakfur Rahaman, Md Tanjul Hoque, Dilip K. Maiti
Summary: A visible-light organophotoredox-catalyzed sulfurization of alkenes and alkynes with aromatic and heteroaromatic thiols using eco-friendly air (O-2) as the sole oxidant has been developed. This method provides a novel, benign, and metal-free strategy for the difunctionalization of alkenes and alkynes using organophotoredox catalyst Eosin Y. The selective and controlled synthetic approach shows good substrate generality to afford sulfoxides, beta-hydroxysulfoxides, and beta-keto sulfides in high yield and excellent regioselectivity.
Article
Chemistry, Organic
Shobhon Aich, Rajesh Nandi, Nirbhik Chatterjee, Krishnanka S. S. Gayen, Subhasis Pal, Dilip K. K. Maiti
Summary: We developed an efficient I-2-catalyzed strategy for the synthesis of functionalized alpha-amidohydroxyketones and symmetrical and unsymmetrical bisamides using benzimidate scaffolds and moist-DMSO. The broad substrate scope and moderate yields are the key advantages of this approach. High-resolution mass spectrometry and labeling experiments provided evidence for the mechanism, and H-1 nuclear magnetic resonance titration revealed the recognition property of the synthesized compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Nanoscience & Nanotechnology
Krishna Chattopadhyay, Manas Mandal, Dilip Kumar Maiti
Summary: Metal-organic frameworks (MOFs) are ideal materials for designing smart biotechnological tools, such as fluorescence-based biosensing platforms for virus detection and excellent antibacterial activity for sustained release of active biocidal agents.
ACS APPLIED BIO MATERIALS
(2021)
Article
Chemistry, Applied
Manas Kumar Mandal, Manas Barai, Habiba Sultana, Emili Manna, Dulal Musib, Dilip Kumar Maiti, Amiya Kumar Panda
Summary: The study investigates the aggregation behavior of SDS in two different IL solutions, revealing a synergistic interaction between ILs and SDS leading to micellization. The size and aggregation number of micelles increase with IL concentration, attributed to the influence of IL cations, forming larger aggregates. This research sheds light on the fundamentals of IL-induced micellization and its practical applications.
JOURNAL OF OLEO SCIENCE
(2021)
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)
