☆ 4.5 Article

Condition based divergence in synthesis of tetrahydrobenzo[b]pyrans

RESEARCH ON CHEMICAL INTERMEDIATES (2016)

期刊

RESEARCH ON CHEMICAL INTERMEDIATES

卷 42, 期 6, 页码 5779-5787

出版社

SPRINGER

DOI: 10.1007/s11164-015-2403-9

关键词

Aromatic aldehydes; Malononitrile; Dimedone; Ultrasonication; Green chemistry; Tetrahydrobenzo[b]pyrans

类别

Chemistry, Multidisciplinary

向作者/读者索取更多资源

Protocol

Reagent

摘要

An environmentally benign novel strategy is developed for the synthesis of tetrahydrobenzo[b]pyrans by using thiamine mononitrate as a green catalyst, with the help of a conventional as well as non-conventional energy source. Synthesis of tetrahydrobenzo[b]pyrans is achieved by one pot condensation of aromatic aldehydes, malononitrile and dimedone in a water-ethanol system. Use of aqueous reaction media, mild conditions, water stable catalyst and energy plummeting process as well as excellent yield, are the key features in completing the reaction. This method excludes the use of volatile organic solvents, tedious workup and column chromatographic purification of compounds, making the method greener, convenient and superior. [GRAPHICS] .

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

4.5

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, Applied

Introducing rGO@Fe3O4@Ni as an efficient magnetic nanocatalyst for the synthesis of tetrahydrobenzopyranes via multicomponent coupling reactions of dimedone, malononitrile, and aromatic aldehydes

Mozhgan Esmati, Behzad Zeynizadeh

Summary: The study investigated the synthesis and characterization of modified GO and rGO@Fe3O4@Ni composite systems. Various analytical techniques were employed to characterize the prepared nanomaterials, and the catalytic activities of different materials were compared in multicomponent coupling reactions. The efficient magnetic nanocatalyst rGO@Fe3O4@Ni was successfully applied to facilitate the reactions, showing sustainable catalytic activity over multiple reaction cycles.

APPLIED ORGANOMETALLIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Green multicomponent approach to novel 5-[(2H-Pyran-3-yl)(aryl)methyl]-1,3-dimethylpyrimidines

Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Artem N. Fakhrutdinov, Michail N. Elinson

Summary: Multicomponent green methodologies play an important role in organic synthesis by efficiently synthesizing compounds using simple and environmentally friendly catalysts and solvents, without the need for complex purification procedures.

JOURNAL OF HETEROCYCLIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

The Immobilized Zirconocene Chloride on Magnetite-reduced Graphene Oxide: A Highly Efficient and Reusable Heterogeneous Nanocatalyst for One-pot Three-component Synthesis of Tetrahydrobenzo[b]pyrans and Dihydropyrano[3,2-c]chromenes

Massood Bayzidi, Behzad Zeynizadeh

Summary: The synthesis and characterization of functionalized magnetite reduced graphene oxide (rGO@Fe3O4) with zirconocene dichloride as rGO@Fe3O4@ZrCp2Cl2 is described in this paper. The prepared magnetic nanomaterial showed excellent catalytic activity for the synthesis of tetrahydrobenzo[b]pyran and Dihydropyrano[3,2-c]chromenes derivatives through a multicomponent reaction. The recovery and reusability of the nanocatalyst were also examined.

CHEMISTRYSELECT (2022)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Tetrahydrobenzo[b]pyrans Catalyzed by 1,3-dibenzyl-1H-benzo[d]imidazole-3-ium Chloride

Ali Moradi Delfani, Hamzeh Kiyani, Mehdi Zamani

Summary: A series of tetrahydrobenzo[b]pyran derivatives were successfully synthesized through three-component reactions, with high yields and relatively shorter reaction times. The optimal reaction conditions were found to be a water-ethanol solvent system, a reaction temperature of 60(o)C, and a 5 mol% loading of the imidazolium catalyst. This method exhibits operational simplicity, no need for chromatographic purification, and avoidance of hazardous solvents.

CURRENT ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Applied

Synthesis of GO and rGO@Fe3O4@Ni as remarkable nanocatalyst systems for solvent-free and chemoselective coupling reactions of dimedone with aromatic aldehydes

Mozhgan Esmati, Behzad Zeynizadeh

Summary: Modified graphene oxide and composite nanomaterial were synthesized and applied as catalysts in multicomponent coupling reactions, showing efficient catalytic activity and good reusability.

APPLIED ORGANOMETALLIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chitosan-ZnO: An Efficient and Recyclable Polymer Incorporated Hybrid Nanocatalyst to Synthesize Tetrahydrobenzo[b]pyrans and Pyrano[2,3-d]pyrimidinonesunder Microwave Expedition

Aravind R. Nesaragi, Tilak Gasti, Tukaram Metre, Ashish Anand, Ravindra R. Kamble, Ravindra B. Chougale, Rangappa S. Keri

Summary: A facile and efficient method for the synthesis of pyran annulated heterocycles using Chitosan-Zinc oxide hybrid nanocatalyst has been developed. This protocol allows for easy operation, convenient work up, and high yields, as well as explores the application of modified polymeric substrates in organic synthesis.

CHEMISTRYSELECT (2022)

添加到收藏夹

Article Chemistry, Physical

Halloysite Nanoclay with High Content of Sulfonic Acid-Based Ionic Liquid: A Novel Catalyst for the Synthesis of Tetrahydrobenzo[b]pyrans

Samahe Sadjadi, Fatemeh Koohestani, Neda Abedian-Dehaghani, Majid M. Heravi

Summary: A novel heterocyclic ligand with multi imine sites was introduced onto the surface of amino-functionalized halloysite support to provide high loading of ionic liquid as a metal-free Bronsted acid catalyst for promoting the synthesis reaction of aldehydes, dimedone and malononitrile. The catalyst exhibited excellent catalytic performance and stability upon recycling.

CATALYSTS (2021)

添加到收藏夹

Article Chemistry, Physical

Modified Agro Waste-Derived Nano-silica for Synthesizing Tetrahydrobenzo[b]pyrans

Pouya Taheri, Mahmood Tajbakhsh, Zari Fallah

Summary: This research utilized rice husk and cotton ball ashes as sources of silica nanoparticles and modified them using metformin and copper acetate. Diverse tetrahydrobenzopyran derivatives were produced with excellent yields in a short reaction time. A comparison was also made between the catalytic behavior of the prepared waste-based nanocatalysts and that derived from commercial-grade nano-silica.

CATALYSIS SURVEYS FROM ASIA (2023)

添加到收藏夹

Article Chemistry, Physical

A new heterogeneous catalyst of triple superphosphate/titanium tetrachloride is used for the synthesis of 1,8-dioxooctahydroxanthenes and tetrahydrobenzo[b]pyrans

Youssef Merroun, Soukaina Chehab, Achraf El Hallaoui, Taoufiq Guedira, Said Boukhris, Abdelaziz Souizi, Rachida Ghailane

Summary: Titanium phosphate catalyst (TiCl4/TSP) was synthesized using a simple impregnation method and characterized using FT-IR, XRD, SEM, and EDX techniques. The catalytic activity was tested for the synthesis of tetrahydrobenzo[b]pyrans and 1,8-dioxooctahydroxanthenes derivatives under environmentally friendly conditions, resulting in excellent yields (90-97%) within 5-15 minutes. The catalyst showed stability for up to five consecutive cycles without significant loss of catalytic reactivity.

JOURNAL OF MOLECULAR STRUCTURE (2023)

添加到收藏夹

Article Polymer Science

One-Pot, Green Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by ZnFe2O4 Nanoparticles an Efficient Nanocatalyst

A. K. Mhaske, A. G. Gadhave, A. G. Dholi, B. K. Uphade

Summary: In this study, zinc ferrite nanoparticles were synthesized in the presence of lemon juice and characterized using various techniques. These nanoparticles were then used as nanocatalysts for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. This green synthetic approach offers important advantages such as the use of non-toxic substances and high yields in a short reaction time.

JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

A green, facile, and one-pot synthesis of 2-amino-4H-pyran derivatives using tungstate sulfuric acid as a solid acid catalyst

Lida Rohani, Bahador Karami, Mahnaz Farahi

Summary: In this study, 2-amino-4H-pyran derivatives were synthesized using tungstate sulfuric acid as a recyclable solid acid catalyst, demonstrating good to excellent yields under mild conditions. The catalyst proved to be low-cost, non-toxic, and reusable, with the ability to maintain its activity over multiple cycles of use.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Green and Effective Preparation of α-Hydroxyphosphonates by Ecocatalysis

Pola Cybulska, Yves-Marie Legrand, Alicja Babst-Kostecka, Sebastien Diliberto, Anna Lesniewicz, Erwan Oliviero, Valerie Bert, Clotilde Boulanger, Claude Grison, Tomasz K. Olszewski

Summary: A green and effective approach for the synthesis of structurally diversed alpha-hydroxyphosphonates via hydrophosphonylation of aldehydes under solventless conditions and promoted by biosourced catalysts Eco-MgZnOx is presented. The ecocatalysts were prepared from Zn-hyperaccumulating plant species Arabidopsis halleri, with simple and benign thermal treatment of leaves rich in Zn, and without any further chemical treatment. The study demonstrates the potential use of the ecocatalysts in hydrophosphonylation of aldehydes, leading to various alpha-hydroxyphosphonate derivatives, which are critical building blocks in the modern chemical industry.

MOLECULES (2022)

添加到收藏夹

Article Chemistry, Organic

A New Avenue to One-Pot Four-Component Synthesis of Spiro[indoline-3,4'-quinoline] Derivatives Using DABCO as a Green Catalyst

Suresh Kumar Maury, Sundaram Singh

Summary: A simple, efficient, and green method has been developed for the synthesis of spiro[indoline-3,4'-quinoline] derivatives. The method uses isatin, ethyl cyanoacetate/malononitrile, dimedone, and aniline as starting materials, with the green catalyst DABCO and green solvent ethanol. The method provides good to exceptional yields in a short reaction time and has a broad substrate scope, including gram scale reactions.

SYNTHESIS-STUTTGART (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Novel and sustainable synthesis of tetrahydrobenzo[b]pyrans using magnetic zinc ferrites modified SBA-15 supported ionic liquids as efficient and reusable catalysts

Yu Lin Hu, Jing Rui Li, Chen Chen, Xiao Bing Liu, Qi Rong

Summary: A series of magnetic zinc ferrites modified SBA-15 supported ionic liquids have been synthesized and evaluated as effective catalysts for the one-pot multi-component reaction. The most active and suitable catalyst efficiently produced tetrahydrobenzo[b]pyrans in high to excellent yields at room temperature. The catalyst exhibited excellent stability and recyclability, making it a promising option for sustainable catalysis.

SUSTAINABLE CHEMISTRY AND PHARMACY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

A facile and efficient synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives using phosphate fertilizers MAP, DAP, and TSP as heterogeneous catalysts

Soukaina Chehab, Youssef Merroun, Tourya Ghailane, Rachida Ghailane, Said Boukhris, Brahim Lakhrissi, Abdelaziz Souizi

Summary: A method for the synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives using three phosphate fertilizers as catalysts has been successfully demonstrated with high catalytic activity. These fertilizers can be reused multiple times, contributing to the development of green chemistry.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Green synthesis and inhibitory effect of novel quinoline based thiazolidinones on the growth of MCF-7 human breast cancer cell line by G2/M cell cycle arrest

Vidya S. Dofe, Aniket P. Sarkate, Rajaram Azad, Charansingh H. Gill

RESEARCH ON CHEMICAL INTERMEDIATES (2018)

添加到收藏夹

Article Chemistry, Organic

β-Cyclodextrin catalyzed access to fused 1,8-dihydroimidazo[2,3-b]indoles via one-pot multicomponent cascade in aqueous ethanol: Supramolecular approach toward sustainability

Amol S. Nipate, Chetan K. Jadhav, Asha Chate, Kanchan S. Taur, Charansingh H. Gill

JOURNAL OF HETEROCYCLIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Organic

Multicomponent reactions and supramolecular catalyst: A perfect synergy for eco-compatible synthesis of pyrido[2,3-d]pyrimidines in water

Asha V. Chate, Ankita S. Kulkarni, Chetan K. Jadhav, Amol S. Nipte, Girabala M. Bondle

JOURNAL OF HETEROCYCLIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate

Chetan K. Jadhav, Amol S. Nipate, Asha Chate, Vishal D. Songire, Anil P. Patil, Charansingh H. Gill

ACS OMEGA (2019)

添加到收藏夹

Article Chemistry, Organic

Ionic liquid catalyzed one-pot multi-component synthesis of fusedpyridine derivatives:A strategyfor green and sustainable chemistry

Chetan K. Jadhav, Amol S. Nipate, Asha V. Chate, Anil P. Patil, Charansingh. H. Gill

JOURNAL OF HETEROCYCLIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Room temperature ionic liquid promoted improved and rapid synthesis of highly functionalized imidazole and evaluation of their inhibitory activity against human cancer cells

Chetan K. Jadhav, Amol S. Nipate, Asha V. Chate, Pratiksha M. Kamble, Ganesh A. Kadam, Vidya S. Dofe, Vijay M. Khedkar, Charansingh H. Gill

Summary: This study utilized an ionic liquid as a catalyst and green solvent for efficient synthesis of tetra- and trisubstituted imidazole scaffolds, resulting in high yields and purity of products. The advantage of this method in gram-scale synthesis and the potent cytotoxic activity of selected compounds against human cancer cell lines were highlighted.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Organic

β-Cyclodextrin: An Efficient Supramolecular Catalyst for the Synthesis of Pyranoquinolines Derivatives under Ultrasonic Irradiation in Water

Chetan K. Jadhav, Amol S. Nipate, Asha V. Chate, Charansingh. H. Gill

Summary: An innovative method for the synthesis of 2-amino-4H-pyranoquinolines has been developed, utilizing beta-cyclodextrin as a reusable supramolecular catalyst in a one-pot three-component reaction catalyzed under ultrasound irradiation in an aqueous medium. The tandem process allows for efficient and convenient synthesis of target products meeting pharmaceutical chemistry requirements.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis and In Vitro Anticancer Activities of New 1,4-Disubstituted-1,2,3-triazoles Derivatives through Click Approach

Amol S. Nipate, Chetan K. Jadhav, Asha Chate, Tejshri R. Deshmukh, Aniket P. Sarkate, Charansingh H. Gill

Summary: In this study, a new series of compounds were synthesized using click chemistry approach and analyzed using various spectroscopic techniques. The cytotoxicity assay revealed that compound 5b exhibited the most potent anticancer activity, while compounds 5a and 5q also showed significant anticancer effects compared to the reference drug Adriamycin.

CHEMISTRYSELECT (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Triethylammonium Hydrogen Sulfate [Et3NH][HSO4]-Catalyzed Rapid and Efficient Multicomponent Synthesis of Pyrido[2,3-d]pyrimidine and Pyrazolo[3,4-b]pyridine Hybrids

Chetan Jadhav, Amol Nipate, Asha Chate, Charansingh Gill

Summary: An operationally simple method for the assembly of pyrido[2,3-d]pyrimidine and pyrazolo[3,4-b]pyridine derivatives has been developed, achieving excellent yields and high purity. The study found that using 1 mmol of the ionic liquid catalyst under solvent-free conditions at 60 degrees Celsius is the optimal reaction parameter for constructing fused pyridine and pyrimidine derivatives. The methodology showed promising results under gram-scale conditions, suggesting potential applicability in both industrial and academic settings in the future.

ACS OMEGA (2021)

添加到收藏夹

Article Chemistry, Organic

Rapid Multicomponent Tandem Annulation in Ionic Liquids: Convergent Access to 3-Amino-1-Alkylpyridin-2(1H)-One Derivatives as Potential Anticancer Scaffolds

Chetan K. Jadhav, Amol S. Nipate, Asha Chate, Makrand Kulkarni, Vidya S. Dofe, Charansingh H. Gill

Summary: An efficient one-pot multicomponent synthesis of 3-amino-1-alkylpyridin-2(1H)-ones using 1,8-diazabicyclo [5,4,0] undec-7-enium acetate [DBUH][OAc] ionic liquid as a green solvent medium was achieved with mild conditions and outstanding conversion rates. The recyclability and recovery of the ionic liquid make this protocol environmentally desirable, and the synthesized compounds showed promising in vitro antitumor activity against human cancer cell lines.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

添加到收藏夹

Article Chemistry, Organic

An Organocatalytic Newer Synthetic Approach toward the Access of Dihydropyrido[2,3-d] Pyrimidine in Water: A Perfect Synergy for Eco-compatible Organic Synthesis

Chetan K. Jadhav, Amol S. Nipate, Asha V. Chate, Charansingh H. Gill

Summary: A simple and effective protocol for synthesizing dihydropyrido[2,3-d]pyrimidine derivatives using 2-aminoethanesulfonic acid in water was presented. This method produced uracil annulated heterocycles with good to excellent yields, offering operational simplicity, easy workup, superior green credentials, and the ability to reuse the catalyst multiple times without significant loss in activity.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

添加到收藏夹

Article Chemistry, Organic

Microwave-Assisted Chemistry: New Synthetic Application for the Rapid Construction of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives in Diisopropyl Ethyl Ammonium Acetate

Chetan K. Jadhav, Amol S. Nipate, Asha Chate, Makrand Kulkarni, Charansingh H. Gill

Summary: In this study, bioactive compounds were successfully synthesized using task-specific ionic liquids as catalysts. The method offers mild reaction conditions, high recyclability, and environmental friendliness.

POLYCYCLIC AROMATIC COMPOUNDS (2023)

添加到收藏夹

Article Chemistry, Organic

An Efficient One-Pot Green Protocol for the Synthesis of Dihydrochromeno[4,3-b]Pyrazolo[4,3-e]Pyridin-6(7H)-Ones Mediated by Diisopropyl Ethyl Ammonium Acetate at Room Temperature

Makrand Kulkarni, Chetan K. Jadhav, Amol S. Nipate, Sarita Bhutada, Charansingh H. Gill, Bhausaheb K. Magar

Summary: A green synthesis method has been developed to efficiently access pharmaceutically relevant functionalized coumarin-pyrazole molecular hybrids. This new procedure offers high yields, short reaction times, simple experimental and work-up procedures, mild reaction conditions and environmental friendliness, along with an economically available catalyst.

POLYCYCLIC AROMATIC COMPOUNDS (2023)

添加到收藏夹

Article Chemistry, Organic

Synthesis and Antimicrobial Activity of New Carbohydrazide Bearing Quinoline Scaffolds in Silico ADMET and Molecular Docking Studies

Amol S. Nipate, Chetan K. Jadhav, Asha V. Chate, Prashant P. Dixit, Prachi Sharma, Charansingh H. Gill

Summary: A series of fluorine-containing quinoline analogues, known as hybrid Schiff bases (6a-o), were successfully synthesized through a facile and efficient conventional method. These compounds were developed via the condensation of a quinoline-4-carbohydrazide intermediate and aromatic aldehydes using ethanol as a solvent. All synthesized compounds (6a-o) exhibited good yields ranging from 76% to 84%. The synthesized compounds were comprehensively characterized using various spectroscopic techniques, including FT-IR, H-1 NMR, C-13 NMR, and Mass spectroscopy. Additionally, the antifungal and antibacterial activity of the newly synthesized hybrid Schiff bases (6a-o) were evaluated. Compounds 6a-d showed promising antibacterial activity, while compound 6b exhibited effectiveness against the fungal pathogen Aspergillus niger. Compound 6a was found to inhibit the visible growth of Staphylococcus aureus ATCC 6538 at a low concentration with a minimum inhibitory concentration of 340 μg/.

POLYCYCLIC AROMATIC COMPOUNDS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rapid Construction of Substituted Dihydrothiophene Ureidoformamides at Room Temperature Using Diisopropyl Ethyl Ammonium Acetate: A Green Perspective

Chetan K. Jadhav, Amol S. Nipate, Asha Chate, Vidya S. Dofe, Jaiprakash N. Sangshetti, Vijay M. Khedkar, Charansingh H. Gill

ACS OMEGA (2020)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.