Article
Chemistry, Organic
Yuhang Xue, Jianbo Gan, Naili Luo, Cunde Wang
Summary: In this study, a DABCO-promoted cyclization reaction of substituted 2-amino-4H-chromen-4-ones with substituted 2,6-dibenzylidenecyclohexan-1-ones was investigated. Under mild conditions, this reaction provided a novel and efficient access to the 7,8,9,10tetrahydro-12H-chromeno[2,3-b]quinolin-12-ones in good yields, with predominantly E-selective exocyclic double bond.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Deepak Ranjan Mishra, Bhabani Shankar Panda, Sabita Nayak, Seetaram Mohapatra, Chita Ranjan Sahoo, Rabindra Nath Padhy
Summary: An efficient synthesis of a series of 4-((2H-chromen-3-yl)/(2-phenyl-2H-chromen-3-yl)methylene)-3-methylisoxazol-5(4H)-ones has been developed. The compounds were synthesized via one-pot multicomponent addition of ethyl acetoacetate, hydroxylamine hydrochloride, and 2H-chromene-3-carbaldehydes using DABCO as the organocatalyst. The synthesized compounds showed potential inhibitory activity against E. coli.
Article
Chemistry, Organic
Khadhar Navaz Umar Basha, Shanthi Gnanamani, Prakash Shanmugam, Sujatha Venugopal, Sangeetha Murthy, Balagurunathan Ramasamy
Summary: The study presents a simple and convenient one-pot synthesis method for the preparation of 3-(1H-indole-3-carbonyl)-2H-chromen-2-one derivatives with high yields and wide substrate scope. The synthesized compounds exhibit good radical scavenging ability, reducing power, as well as antibacterial and antifungal activities, showing potential for various applications.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Toshiaki Shimasaki, Kurumi Kobayashi, Takayuki Kitanou, Tomohiro Oki, Tenta Ishikawa, Naoto Asano, Tetsuo Iwanaga, Naozumi Teramoto, Mitsuhiro Shibata
Summary: 3-(4-(Arylethynyl)phenyl)-7-(diethylamino)-2H-chromen-2-ones 1a-1d were synthesized via Pd/Cu-catalyzed Sonogashira cross-coupling reactions. Their photophysical properties, including fluorescence properties in different states, were systematically studied, revealing different fluorescence quantum yields. Theoretical and electrochemical studies showed the importance of compound structures in determining their fluorescence properties.
Article
Chemistry, Organic
Haiwen Li, Junhu Xin, Yuhang Xue, Cunde Wang
Summary: A pseudo-three-component annulation reaction was investigated to access polysubstituted 5H-chromeno[2,3-b]pyridines. This reaction involved a sequential intermolecular addition/cyclization/epoxidation/ring opening/aromatization sequence, providing an efficient and atom economical approach for the synthesis of 3-hydroxy-5H-chromeno[2,3-b]pyridines from readily available substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jianbo Gan, Junhu Xin, Yuhang Xue, Cunde Wang
Summary: A formal [3+3] cascade annulation strategy has been developed for the synthesis of 2-arylchromeno[2,3-b]pyridinones. The strategy provides a novel and atom-economical method for accessing a broad range of chromeno[2,3-b]pyridine derivatives in good yields with good functional-group tolerance, highlighting the practicality of this synthetic transformation.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Lv You, Li Kun, Hao Ze-Sheng, Tatiana A. Kalinina, Tatiana Glukhareva, Fan Zhi-Jin
Summary: A kind of coumarin derivatives were successfully synthesized and structurally characterized. In vitro bioassay showed good activity against various fungi and in vivo screening demonstrated effective antifungal efficacy of the compounds. This study suggests that the combination of isothiazole with coumarin can be a promising approach for novel fungicide development.
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
(2021)
Article
Chemistry, Physical
Hong-Bo Tan, Yuan-Hui Yu, Ze-Hui Qi, Xu Zhang, Zhi-Gang Xu, Dian-Yong Tang, Zhong-Zhu Chen, Bo-Chu Wang, Xian-You Qu
Summary: This paper describes an efficient, concise, and environmentally friendly photochemical vinylogous aldol reaction for the diastereoselective synthesis of novel trans-3-(2-benzoylstyryl)-4H-chromen-4-ones using readily available methylbenzophenone and 3-formylchromone without any bases, metals, or other catalysts. The products were obtained with perfect diastereoselectivity under UV LED (365 nm) irradiation at room temperature in 9 hours. NMR spectra analysis (1D-NMR and 2D-NMR) was conducted to discuss the special patterns of alkene protons and confirm the trans-conformation, which was further confirmed by single crystal X-ray analysis, NMR, HRMS, and XRD analysis. XRD analysis of 3a provided insights into the improved planarity of the alkene moiety compared to the benzophenone moiety in the title compounds.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Andrey N. Komogortsev, Boris Lichitsky, Valeriya G. Melekhina, Mikhail E. Minyaev
Summary: This study demonstrates the feasibility of cine-substitution for 3-nitrocoumarins for the first time and develops a novel efficient protocol for the preparation of substituted 2H-chromen-2-ones. The reaction is simple and proceeds under mild conditions, allowing for easy purification of the products.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Palani Natarajan, Priya, Deachen Chuskit
Summary: In this study, a method for the direct synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters using nitrogen doped graphene as an oxidant in a watery medium at room temperature has been reported. The method is environmentally friendly, sustainable, practical, and energy efficient, and does not use harmful nitro sources. Additionally, the nitrogen doped graphene used can be easily recovered and reused.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ekaterina E. Khramtsova, Ekaterina A. Lystsova, Evgeniya V. Khokhlova, Maksim V. Dmitriev, Andrey N. Maslivets
Summary: The 3-hydroxy-1,5-dihydro-2H-pyrrol-2-one motif is valuable in drug discovery, and replacing the 3-oxy fragment with a 3-amino one can significantly impact the biological effect of compounds. Developing approaches to 3-amino-1,5-dihydro-2H-pyrrol-2-ones is of significant interest, and a new approach involving thermal decomposition of urea derivatives was successfully developed in this study.
Article
Chemistry, Organic
Shengfei Dai, Ke Yang, Yanqi Luo, Ziyuan Xu, Zhi Li, Zhengyi Li, Bijin Li, Xiaoqiang Sun
Summary: Diverse transformations using Selectfluor as a catalyst have been developed for the synthesis of 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles. The selective cleavage of C-S and C-H bonds can be controlled by different reaction conditions. Notably, this study demonstrates the first example of using Selectfluor as a source to construct 2,3-dihydrobenzothiazin-4-ones.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Pankaj Khairnar, Yin-Hsiang Su, Athukuri Edukondalu, Wenwei Lin
Summary: An enantioselective synthesis of spiropyrazolone-fused cyclopenta[c]chromen-4-ones is demonstrated via a (3+2) cycloaddition reaction using cinchona-alkaloid derived hydrogen-bonding catalyst. The method provides high yields of adducts with five contiguous stereocenters, including a spiro all-carbon quaternary stereocenter with good to excellent stereoselectivities. The one-pot methodology can also be scaled up effectively.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amr Elagamy, Laila K. Elghoneimy, Reem K. Arafa, Ramendra Pratap
Summary: A simple and efficient method for the synthesis of flavones was achieved by selective sulfide LiebeskindSrogl cross-coupling reaction, where 2-(methylthio)-4H-chromen-4-ones and 3-halo-2-(methylthio)-4H-chromen-4-ones were reacted with arylboronic acids. This method allows direct installation of various aryl groups to the chromone ring. The structures of the synthesized compounds were confirmed by spectroscopic analysis.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Florian Sachse, Christoph Schneider
Summary: A novel protocol for the direct synthesis of 1,3-oxathiolan-5-ones based on the (3+2)-cycloaddition between thioketones and acetylenedicarboxylic acid was reported. The products were obtained in a one-pot reaction with short reaction times and typically very good yields. The product structure was confirmed by X-ray diffraction analysis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)