☆ 4.4 Article

Synthesis of 2-selenoxoperhydro-1,3-selenazin-4-ones via diselenocarbamate intermediates

TETRAHEDRON (2009)

期刊

TETRAHEDRON

卷 65, 期 24, 页码 4775-4780

出版社

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tet.2009.04.004

关键词

Selenium; Selenocarbamate; Isoselenocyanate; 1,3-Selenazine

类别

Chemistry, Organic

向作者/读者索取更多资源

Protocol

Reagent

摘要

The reactions of the diselenocarbamates, generated from isoselenocyanates and sodium hydroselenide, with acryloyl chlorides afforded 2-selenoxoperhydro-1,3-selenazin-4-ones. The structure of the product was confirmed by X-ray diffraction analysis. (C) 2009 Elsevier Ltd. All rights reserved.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.4

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Organic

One-Pot Four-Component Assembling for Selenoureas

Lai Li, Jiaqi Wu, Linsha Wei, Jianmei Lu, Xuefeng Jiang

Summary: A practical method for constructing unsymmetrical selenoureas and cycloselenoureas was achieved efficiently in one-pot under mild conditions, resulting in the synthesis of several new structures. The compound 1,1-Dimethyl-3-phenylselenourea II, which exhibited good fungicidal activity, was successfully synthesized in gram-scale through this method. The key intermediate isoselenocyanate was further confirmed through control experiments.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Review Chemistry, Physical

Recent Advances in Design and Synthesis of 1,3-Thiaselenolane and 1,3-Thiaselenole Derivatives

Svetlana V. Amosova, Nataliya A. Makhaeva

Summary: This review discusses recent advances in the design and synthesis of five-membered heterocycles containing both sulfur and selenium atoms, specifically 1,3-thiaselenolane and 1,3-thiaselenole derivatives. These heterocyclic systems are of interest as intermediates for organic synthesis and compounds with various useful properties. The review focuses on catalytic reactions and also presents synthetic methods for related 1,4,5,8-diselenadithiafulvalenes based on catalytic cross-coupling reactions. The design and synthesis of 1,3-thiaselenolane and 1,3-thiaselenole derivatives have not been discussed in a separate review before.

CATALYSTS (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

New Organoselenium (NSAIDs-Selenourea and Isoselenocyanate) Derivatives as Potential Antiproliferative Agents: Synthesis, Biological Evaluation and in Silico Calculations

Yousong Nie, Shaolei Li, Ying Lu, Min Zhong, Xiaolong Li, Youhong Zhang, Xianran He

Summary: This study synthesized a series of new organoselenium derivatives and evaluated their inhibitory activity against four types of cancer cell lines. The compounds showed significant inhibitory activity against the cancer cell lines, especially HeLa and MCF-7 cells. The study also investigated the mechanism of apoptosis induction and the redox properties of the derivatives. Molecular docking revealed an interaction with the active site of thioredoxin reductase 1, which predicted the antiproliferative activity of the compounds.

MOLECULES (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO2: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

Ibakyntiew D. Marpna, O. Risuklang Shangpliang, Kmendashisha Wanniang, Baskhemlang Kshiar, Tyrchain Mitre Lipon, Badaker M. Laloo, Bekington Myrboh

Summary: A novel method for the synthesis of fused 1,3-dioxolanes was developed, involving the self-condensation of glyoxal generated in situ by oxidation of acetophenones with SeO2 in the presence of trifluoroacetic acid. This reaction allows for the construction of four C-O bonds simultaneously, resulting in architecturally novel oxygen-containing heterocycles from readily available ketones using affordable shelf reagents and simple reaction conditions.

ACS OMEGA (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

A multicomponent reaction of isocyanides, selenium powder and 3-aminooxetanes in pure water: green and efficient synthesis of 1,3-selenazolines

Huan Liu, Zi-Lin Ye, Zhong-Jian Cai, Shun-Jun Ji

Summary: In this study, a novel, efficient and metal-free multicomponent reaction of isocyanides, selenium powder and 3-aminooxetanes was reported. The reaction used selenium powder as the selenium source and H2O as the sole reaction medium, resulting in a series of 1,3-selenazolines under mild conditions. The transformation demonstrated good functional group compatibility, broad substrate scope and high atom economy, while avoiding the use of unstable and toxic selenium agents, additional phase transfer catalysts and transition-metal catalysts, aligning with the concept of green organic synthesis. Additionally, the obtained selenazolines were easily applied to the derivatization of biologically active molecules, providing a new avenue for the synthesis of drug-like organoselenium compounds.

GREEN CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Synthesis of 1,3-diselenyl-dihydroisobenzofurans via electrochemical radical selenylation with substituted o-divinylbenzenes and diselenides

Ying Wang, Ning Xu, Weiwei Li, Jiaojiao Li, Yijun Huo, Wenrong Zhu, Qiang Liu

Summary: An efficient electrochemical method has been developed for the direct synthesis of complicated 1,3-diselenyl-dihydroisobenzofurans from substituted o-divinylbenzenes and diselenides under external oxidant free conditions at room temperature. A radical mechanism is proposed for this novel and practical transformation.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Applied

Synthesis of Quinolines and 2-Functionalized Quinolines by Difluorocarbene Incorporation

Ben-Jie Jiang, Song-Lin Zhang

Summary: A general method is developed for the synthesis of quinolines and C2-functionalized quinolines from ortho-alkenyl anilines using a difluorocarbene precursor. The method involves the in-situ generation of isocyanides from primary aniline and difluorocarbene, which then undergo alpha-addition by neighboring alkenyl groups to form the quinoline ring. In the presence of Se, selenoisocyanate intermediates are generated, leading to the synthesis of 2-SeH quinolines. The method allows for the modular synthesis of various C2-functionalized quinolines in one step, using readily available starting compounds.

ADVANCED SYNTHESIS & CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Organic

1-(3-Isoselenocyanatopropyl)adamantane

Dmitry Pitushkin, Vladimir Burmistrov, Gennady Butov

Summary: The title compound, 1-(3-isoselenocyanatopropyl)adamantane, was synthesized for the first time by a two-stage reaction using 3-(adamantan-1-yl)propan-1-amine and 1-(3-isocyanopropyl)adamantane as intermediates. The product was characterized by NMR, GC-MS, and elemental analysis.

MOLBANK (2023)

添加到收藏夹

Article Chemistry, Organic

Electrochemical oxidative cyclization of alkenes, boronic acids, and dichalcogenides to access chalcogenated boronic esters and 1,3-diols

Changfeng Huang, Jijing Hu, Guangxian Chen, Minjian Wu, Hua Cao, Xiang Liu

Summary: A sustainable and environmentally benign electrochemical oxidative three-component cyclization has been developed under metal-free and oxidant-free conditions, providing an efficient approach for the formation of C-Se/S and C-O bonds. A series of chalcogenated boronic esters were obtained with a broad substrate scope, and easily converted to chalcogenated 1,3-diols in good yields under mild conditions.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

PIFA-mediated selenylative spirocyclization of indolyl ynones: facile access to selenated spiro[cyclopentenone-1,3′-indoles]

Zhichao Chen, Jingjing Li, Wenting Weng, Xiaolan Xie, Jian Lei

Summary: A fast selenylative spirocyclization reaction mediated by PIFA has been developed for the synthesis of selenated spiro[cyclopentenone-1,3'-indoles]. The reaction involves the generation of reactive RSeOCOCF3 species from diselenides with PIFA, enabling an electrophilic dearomative cascade cyclization. This protocol provides a facile and efficient method with broad functional group tolerance.

RSC ADVANCES (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

An Organofluorine Isoselenocyanate Analogue of Sulforaphane Affects Antimetabolite 5-Fluorouracil's Anticancer Activity: A Perspective for New Combinatory Therapy in Triple-Negative Breast Cancer

Malgorzata Milczarek, Tomasz Cierpial, Piotr Kielbasinski, Milena Malecka-Gieldowska, Marta Switalska, Joanna Wietrzyk, Maciej Mazur, Katarzyna Wiktorska

Summary: The combination of 5-fluorouracil and ISC has synergistic effects on triple-negative breast cancer, leading to enhanced antiproliferative effects and safety.

MOLECULES (2023)

添加到收藏夹

Article Chemistry, Organic

Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XV.1 N,N′-(Alkane-α,ω-diyl)bis[N′-(adamantan-1-yl)]selenoureas

Ya. P. Kuznetsov, D. A. Pitushkin, V. V. Burmistrov, G. M. Butov

Summary: A series of N,N'-(alkane-alpha,omega-diyl)bis[N'-(adamantan-1-yl)selenoureas] were synthesized in moderate to high yields by reaction between adamantan-1-yl isoselenocyanate and alkane-alpha,omega-diamines. The synthesized compounds exhibit lower melting points compared to their isosteric analogs containing urea fragments and show promise as inhibitors of human soluble epoxide hydrolase.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Applied

Synthesis of 2-Imino-1,3,4-Selenadiazoles via Tributylphosphine-Mediated Annulation of N-Aroyldiazenes with Isoselenocyanates

Zhengyan Huang, Qianqian Zhang, Xiaofei Yi, Zongxiang Zhao, Wenquan Yu, Junbiao Chang

Summary: A new synthetic strategy for synthesizing 2-imino-1,3,4-selenadiazole derivatives has been proposed, which involves sequential oxidation and a tributylphosphine-promoted annulation reaction. The method has the advantages of absence of transition metals and potential for gram-scale synthesis.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Se-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]4-Chlorobenzoselenolate Attenuates Inflammatory Response, Nociception, and Affective Disorders Related to Rheumatoid Arthritis in Mice

Ethel A. Wilhelm, Paola S. Soares, Angelica S. Reis, Ketlyn P. Motta, Briana B. Lemos, William B. Domingues, Eduardo B. Blodorn, Daniela R. Araujo, Angelita M. Barcellos, Gelson Perin, Mauro P. Soares, Vinicius F. Campos, Cristiane Luchese

Summary: This study evaluated the potential of Se-DMC in a CFA-induced arthritis model in mice, showing its anti-inflammatory, analgesic, and neurobehavioral correction effects. Se-DMC reduced paw edema, decreased expression of inflammatory molecules, restored neurobehavioral deficits induced by CFA, indicating potential therapeutic benefits.

ACS CHEMICAL NEUROSCIENCE (2021)

添加到收藏夹

Article Chemistry, Organic

Synthesis of 1,3-Dioxan-2-ones by Photo-Aerobic Selenium-π-Acid Multicatalysis

Kilian A. Mueller, Carolin H. Nagel, Alexander Breder

Summary: An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters using photo-aerobic selenium-pi-acid multicatalysis is reported. This method directly activates the C-C double bond of homoallylic carbonic acid esters using a pyrylium dye and a diselane, with ambient air as the sole oxidant and visible light as an energy source, without relying on stoichiometric addition of electrophiles or pre-installed leaving groups.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Regioselective and diastereoselective iodocyclization reaction of alkene-thioureas: an efficient approach to bicyclic β-lactams

Dinesh R. Garud, Amol D. Sonawane, Jyoti B. Auti, Navnath D. Rode, Vinod R. Ranpise, Rohini R. Joshi, Ramesh A. Joshi

NEW JOURNAL OF CHEMISTRY (2015)

添加到收藏夹

Article Chemistry, Organic

Synthesis of thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivatives via iodocyclization reaction and a DFT mechanistic study

Amol D. Sonawane, Dinesh R. Garud, Taro Udagawa, Mamoru Koketsu

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Organic

A convenient synthesis of the enantiomerically pure (S)-2,4-dihydroxybutyl-4-hydroxybenzoate using hydrolytic kinetic resolution

Namita A. More, Nitin L. Jadhao, Dinesh R. Garud, Jayant M. Gajbhiye

SYNTHETIC COMMUNICATIONS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of thieno[2,3-c]acridine and furo[2,3-c]acridine derivatives via an iodocyclization reaction and their fluorescence properties and DFT mechanistic studies

Amol D. Sonawane, Dinesh R. Garud, Taro Udagawa, Yasuhiro Kubota, Mamoru Koketsu

NEW JOURNAL OF CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes

Amol D. Sonawane, Yunnus B. Shaikh, Dinesh R. Garud, Mamoru Koketsu

SYNTHESIS-STUTTGART (2019)

添加到收藏夹

Article Chemistry, Medicinal

Non Nucleoside Reverse Transcriptase Inhibitors, Molecular Docking Studies and Antitubercular Activity of Thiazolidin-4-one Derivatives

Trupti S. Chitre, Shital M. Patil, Anagha G. Sujalegaonkar, Kalyani D. Asgaonkar, Vijay M. Khedkar, Dinesh R. Garud, Prakash C. Jha, Sharddha Y. Gaikwad, Smita Kulkarni, Amit Choudhari, Dhiman Sarkar

CURRENT COMPUTER-AIDED DRUG DESIGN (2019)

添加到收藏夹

Article Chemistry, Medicinal

In silico Studies, Synthesis and Antitubercular Activity of Some Novel Quinoline - Azitidinone Derivatives

Trupti S. Chitre, Kalyani D. Asgaonkar, Amrut B. Vikhe, Shital M. Patil, Dinesh R. Garud, Vijay M. Khedkar, Dhiman Sarkar, Laxman U. Nawale, Amar Yeware

Summary: In this study, a series of quinoline derivatives were designed and synthesized as potential anti-tubercular agents, with structural features explored through computational tools. The synthesized compounds showed promising anti-tubercular activity, interacting with MTB ATPase. Further research can be conducted for lead generation based on these results.

CURRENT COMPUTER-AIDED DRUG DESIGN (2021)

添加到收藏夹

Article Chemistry, Applied

Design, Synthesis and Opto-electrochemical Properties of Novel Donor-Acceptor Based 2,3-di(hetero-2-yl)pyrido [2,3-b] pyrazine amine derivatives as Blue-Orange Fluorescent Materials

Suraj S. Mahadik, Dinesh R. Garud, Anuja P. Ware, Subhash S. Pingale, Rajesh M. Kamble

Summary: Novel donor-acceptor type pyrido derivatives were synthesized through palladium-catalyzed reactions, characterized by spectroscopic, electrochemical, and thermal methods, exhibiting efficient emission and charge transport properties suitable for applications in organic electronics.

DYES AND PIGMENTS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

An efficient method for the synthesis of quinoxaline derivatives catalyzed by titanium silicate-1

Pranav S. Chandrachood, Amol R. Jadhav, Dinesh R. Garud, Nirmala R. Deshpande, Vedavati G. Puranik, Rajashree V. Kashalkar

RESEARCH ON CHEMICAL INTERMEDIATES (2020)

添加到收藏夹

Article Chemistry, Physical

Synthesis, optical, electrochemical and theoretical studies of 2,3-Di(pyridin-2-yl)quinoxaline amine derivatives as blue-orange emitters for organic electronics

Suraj S. Mahadik, Dinesh R. Garud, Rahul V. Pinjari, Rajesh M. Kamble

Summary: This study presents the design and synthesis of six new donor-acceptor bipolar compounds, characterized by the use of 2,3-di(pyridin-2-yl)quinoxaline as the acceptor and diaryl/heterocyclic amine donors prepared through palladium-catalyzed Buchwald-Hartwig coupling reaction. These compounds exhibit specific absorption and emission properties in various solvents, with excellent thermal stability and opto-electronic properties, making them suitable for use in opto-electronic devices.

JOURNAL OF MOLECULAR STRUCTURE (2022)

添加到收藏夹

Article Chemistry, Organic

Synthesis, biological evaluation and molecular docking studies of quinoline-conjugated 1,2,3-triazole derivatives as antileishmanial agents

Sandeep R. Tapkir, Rajendra H. Patil, Sharad A. Galave, Ganesh R. Phadtare, Vijay M. Khedkar, Dinesh R. Garud

Summary: In this study, novel quinoline-conjugated 1,2,3-triazole derivatives were synthesized from substituted acetanilides and screened for their antileishmanial activity. Some of these compounds showed potent antileishmanial activity and have the potential to become lead molecules in drug discovery for treating leishmaniasis.

JOURNAL OF HETEROCYCLIC CHEMISTRY (2022)

添加到收藏夹

Article Optics

2,2′,3,3′-Tetrakis(4-bromophenyl)-6,6′-biquinoxaline based novel Donor-Acceptor-Acceptor-Donor (DAAD) Blue-Orange emitting molecules: Opto-electrochemical, AIE and theoretical investigation

Suraj S. Mahadik, Dinesh R. Garud, Mohammed K. Ghadiyali, Sajeev Chacko, Rajesh M. Kamble

Summary: A series of novel donor-acceptor-acceptor-donor biquinoxaline amine derivatives were synthesized using palladium catalyzed reactions. The compounds exhibited good emission properties in different solvents and solid state, making them potential candidates for opto-electronic applications.

JOURNAL OF LUMINESCENCE (2022)

添加到收藏夹

Article Chemistry, Organic

A metal-free isoamyl nitrite mediated efficient synthesis of 1,2,4-oxadiazoles

Sharad A. Galave, Kishorkumar S. Kadam, Amol D. Sonawane, Vaibhav R. Pansare, Dinesh R. Garud

Summary: This article reports a metal-free efficient synthesis of 1,2,4-oxadiazoles mediated by isoamyl nitrite, through a one-pot cycloaddition reaction of aldoximes with nitriles. The structure of the 1,2,4-oxadiazole derivatives was confirmed by spectral analysis. This methodology provides a novel pathway to access 1,2,4-oxadiazole derivatives.

TETRAHEDRON LETTERS (2023)

添加到收藏夹

Article Chemistry, Medicinal

Ruthenium(II)- and copper(I)-catalyzed synthesis of click-xylosides and assessment of their glycosaminoglycan priming activity

Caitlin P. Mencio, Dinesh R. Garud, Yosuke Doi, Yiling Bi, Hariprasad Vankayalapati, Mamoru Koketsu, Balagurunathan Kuberan

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2017)

添加到收藏夹

Article Biology

QSAR, docking studies of 1,3-thiazinan-3-yl isonicotinamide derivatives for antitubercular activity

Trupti S. Chitre, Kalyani D. Asgaonkar, Shital M. Patil, Shiva Kumar, Vijay M. Khedkar, Dinesh R. Garud

COMPUTATIONAL BIOLOGY AND CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Organic

Facile synthesis of quinoxaline catalyzed by iron-based carbon material in water

Fuying Zhu, Yamei Lin

Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.

TETRAHEDRON (2024)

添加到收藏夹

Article Chemistry, Organic

Simple approach towards phosphorus-substituted spiro 1,3,4-thiadiazolines

Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova

Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.

TETRAHEDRON (2024)

添加到收藏夹

Article Chemistry, Organic

Recent advances in the synthesis of 2-cyclopentenones

Jisna Jose, Thomas Mathew

Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.

TETRAHEDRON (2024)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.