Article
Chemistry, Organic
Amitava Rakshit, Hirendra Nath Dhara, Ashish Kumar Sahoo, Tipu Alam, Bhisma K. Patel
Summary: A Pd(II)-catalyzed synthesis of furopyridines has been developed via an unusual N-H/C annulation from beta-ketodinitriles and alkynes. The important features of this method include the participation of both nitrile groups and the concurrent construction of furan and pyridine rings through the formation of multiple bonds. The synthetic applicability is demonstrated through subsequent alterations.
Article
Chemistry, Organic
Christopher Cunningham, Matthew Cloyd, Aimee Phillips, Soha Khan, Katherine Whalen, Tanay Kesharwani
Summary: This study introduces a new environmentally benign iodine-mediated strategy for synthesizing benzo[b]thiophene derivatives in a one-pot reaction process. The method allows for the synthesis of a diverse range of complex structures in high yields, with potential applications in biomedical and organic electronic fields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Michail N. Elinson, Oleg I. Maslov, Artem N. Fakhrutdinov
Summary: In this study, the green chemistry techniques of PASE and one-pot synthesis were applied to efficiently and quickly synthesize Chromeno[2,3-b]pyridines, substances demanded in medicinal and material chemistry. By extending the PASE approach with 'component economy' and involving the solvent as a reactant, O-substituted 5-alkoxy-5H-chromeno[2,3-b]pyridines were synthesized via a two-step transformation. Mechanistic studies aided in optimizing the reaction conditions for high yields (77-93%).
Article
Biochemistry & Molecular Biology
Ida Bocek Pavlinac, Mirna Dragic, Leentje Persoons, Dirk Daelemans, Marijana Hranjec
Summary: A series of novel 2,6-diphenyl substituted imidazo[4,5-b]pyridines were synthesized and evaluated for their biological activity. Certain compounds showed strong antiproliferative activity against cancer cells, with a dose-dependent cell cycle-phase-specific mechanism of action. However, most of the tested compounds showed no antiviral activity.
Article
Chemistry, Organic
Thiago J. Peglow, Ricardo H. Bartz, Thiago Barcellos, Ricardo F. Schumacher, Roberta Cargnelutti, Gelson Perin
Summary: An alternative method for the synthesis of highly substituted 2-aryl-(3-organochalcogenyl)thieno[2,3-b]pyridines was described, using electrophilic species generated in situ from the oxidative cleavage of chalcogen-chalcogen bonds in diorganyl dichalcogenides. The protocol allowed the synthesis of 21 new compounds in good to excellent yields (70-99%) starting from various diorganyl dichalcogenides and 3-(arylethynyl)-2-(alkylthio)pyridines, demonstrating good efficiency in gram-scale synthesis and compatibility with various synthetic transformations such as oxidation, selenylation, and hydrogenation reactions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jie Zhou, Manna Huang, Xinhai Zhu, Yiqian Wan
Summary: A series of novel V-shaped furo[2,3-b]furans have been designed and synthesized, among which one compound showed dual-state emission properties in solution and solid state with high fluorescence quantum yields.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Ricardo Hellwig Bartz, Thiago Jacobsen Peglow, Filipe Penteado, Raquel Guimaraes Jacob, Eder Joao Lenardao, Gelson Perin
Summary: A simple and environment-friendly protocol was described for the synthesis of 2-aryl-(3-organoselanyl)thieno[2,3-b]pyridines, using diorganyl diselenides as selenium source and visible light-promoted selenocyclization reaction.
GREEN CHEMISTRY LETTERS AND REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Hai-Tao Gao, Jun-Kai Ma, Yang-Gen Hu, Hong-Mei Wang
Summary: This paper describes the synthesis of a series of polysubstituted furo[2,3-d]pyrimidinones, including 1,2,4-triazole-fused derivatives, via aza-Wittig reactions of iminophosphoranes under mild conditions.
JOURNAL OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Applied
Zhenli Luo, Ji Yang, Zhen Yao, Jianbo Yang, Lijin Xu, Qian Shi
Summary: A metal-free catalytic protocol using B(C6F5)(3) catalyst has been developed for the diastereoselective synthesis of cis-2,3-disubstituted 1,2,3,4-tetrahydroquinoxalines and cis-2,4-disubstituted 2,3,4,5-tetrahydro-1H-1,5-benzodiazepines. The reaction involves one-pot tandem cyclization/hydrosilylation of easily accessible 1,2-diaminobenzenes and 1,2- and 1,3-diketones with polymethylhydrosiloxane (PMHS), resulting in various substituted products with good yields. The diastereoselectivity of the reaction depends on the choice of hydrosilane, with PMHS showing optimal results.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Tereza Edlova, Hana Dvorakova, Vaclav Eigner, Tomas Tobrman
Summary: Easily available disubstituted cyclobutenes were regioselectively halogenated at the allylic position by means of a reaction with bromine. The regioselectivity of bromination is controlled by the presence of a carbocation-stabilizing group. The prepared disubstituted 3-bromocyclobutenes were converted into the corresponding disubstituted cyclobutenones. The proposed mechanism behind the bromination reaction was based on the performed experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kseniya Belyaeva, Lina P. Nikitina, Andrey Afonin, Ludmila A. Grishchenko, Boris A. Trofimov
Summary: A convenient method for synthesizing 2-(1-ethoxyalkoxy)-3-cyanoquinolines has been developed, involving functionalization of quinolines with acetals of cyanopropargylic alcohols followed by sequential removal of acetal protection and intramolecular cyclization/hydration to obtain furo[3,4-b] quinolinones in high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Visarapu Malathi, Nissi Sharon, Pannala Padmaja, Deepak Lokwani, Saurabh Khadse, Prashant Chaudhari, Atul A. Shirkhedkar, Pedavenkatagari Narayana Reddy, Vinod G. Ugale
Summary: An efficient synthetic strategy for the synthesis of [1,3]dioxolo[4',5':6,7]chromeno[2,3-b]pyridines was developed. The synthesized compounds showed significant anticonvulsant activity, with one compound (4h) demonstrating good therapeutic/toxicity profile. Molecular dynamic simulation revealed stable interactions between compound 4h and GABA(A) receptor. These findings suggest that these analogs have potential as valid leads for the development of future effective neurotherapeutic agents.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Multidisciplinary
Sumeyye Yalduz, Mehmet Yilmaz
Summary: In this study, furo[2,3-d]pyrido[1,2-a]pyrimidin-4-ones were synthesized by microwave-assisted radical cyclizations. The reaction was performed between 2-hydroxy-4H-pirido[1,2-a]pirimidin-4-ones and conjugated alkenes and phenylacetylene using Mn(OAc)(3) as a catalyst. Different reaction conditions were compared to optimize the reaction. The obtained compounds were characterized using spectroscopic techniques and XRD analysis.
Article
Chemistry, Organic
D. Antonov, M. Dmitriev, A. N. Maslivets
Summary: The reaction between 4,5-dibenzoyl-1H-pyrrole-2,3-diones and methyl 5-aminofuran-2-carboxylate leads to the formation of methyl 4-benzoyl-5-(aminooxalyl)-6-phenylfuro[2,3-b]pyridine-2-carboxylates. This reaction differs from the characteristic reactions with N-unsubstituted five-membered cyclic enamines, providing a convenient preparative method for the synthesis of furo[2,3-b]pyridines.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Michail N. Elinson, Anatoly N. Vereshchagin, Roman A. Novikov, Artem N. Fakhrutdinov
Summary: Some of the most important transformations in organic chemistry are rearrangement reactions, which increase synthetic efficiency and molecular complexity. The development of synthetic strategies involving rearrangement reactions has been a hot topic in the chemistry community. In this work, the thermal rearrangement of 7,9-dihalogen-substituted 5-(2-hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines in DMSO was proposed. Previously unknown compounds were synthesized with high yields (90-99%) and their structures were confirmed using 2D-NMR spectroscopy.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
