Article
Chemistry, Organic
Julia O. Strelnikova, Alexander N. Koronatov, Nikolai Rostovskii, Alexander F. Khlebnikov, Olesya Khoroshilova, Mariya A. Kryukova, Mikhail S. Novikov
Summary: The domino reaction catalyzed by Rh-2(Piv)(4) leads to the formation of N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles, providing a direct and flexible access to the desired compounds.
Article
Chemistry, Multidisciplinary
Mengjuan Li, Jingya Li, Zhiguo Zhang, Liming Chen, Nana Ma, Qingfeng Liu, Xingjie Zhang, Guisheng Zhang
Summary: A palladium(ii)-catalyzed intramolecular oxidative aza-Wacker-type reaction of vinyl cyclopropanecarboxamides has been developed to access a series of conformationally restricted highly substituted aza[3.1.0]bicycles. The reaction proceeds through a typical aza-Wacker reaction mechanism, utilizing oxygen as the terminal oxidant to forge a new C-N bond. The desired fused heterocycles are obtained in moderate yields, and the process shows tolerance towards various functional groups under mild conditions.
Article
Chemistry, Organic
Rafael G. Uceda, Esther Roldan-Molina, Jorge A. R. Navarro, J. Enrique Oltra
Summary: This study explores the use of electron-deficient dienes as substrates in the aza Diels-Alder reaction, showing that the amide group significantly influences the yield of the reaction products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Spectroscopy
Ramil F. Fatykhov, Ainur D. Sharapov, Ekaterina S. Starnovskaya, Yaroslav K. Shtaitz, Maria I. Savchuk, Dmitry S. Kopchuk, Igor L. Nikonov, Grigory V. Zyryanov, Igor A. Khalymbadzha, Oleg N. Chupakhin
Summary: A series of coumarin-pyridine push-pull fluorophores were successfully synthesized through direct C-H functionalization, with 4-alkylcoumarin pyridine derivatives showing good photoluminescence quantum yields, while 4-phenylcoumarin derivatives did not exhibit noticeable fluorescence. Detailed photophysical studies demonstrated the potential of combining different chromophore systems to enhance the properties of new fluorescent compounds.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2022)
Article
Chemistry, Multidisciplinary
Masao Ohashi, Dan Tan, Jiayan Lu, Cooper S. Jamieson, Daiki Kanayama, Jiahai Zhou, K. N. Houk, Yi Tang
Summary: The synthesis of cis-decalin structures using [4 + 2] cycloaddition with high stereoselectivity is challenging. In this study, we investigated the biosynthetic pathway of the fungal natural product fischerin (1) and identified a novel pericyclase, FinI, which catalyzes this reaction. The cocrystal structure of FinI, a predicted O-methyltransferase, with the product and SAM provides valuable insights into the natural formation of cis-decalin.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Wei Cao, Yingchao Dou, Cyrille Kouklovsky, Guillaume Vincent
Summary: The first total synthesis of the monoterpene indole alkaloids ophiorrhine A is reported via a late stage bioinspired intramolecular Diels-Alder cycloaddition. The synthesis includes the construction of the indolopyridone moiety, cyclodehydration, and the desired spontaneous intramolecular Diels-Alder cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Po Yuan, Christa K. G. Gerlinger, Jan Herberger, Tanja Gaich
Summary: The first asymmetric synthesis of pepluanol A was achieved using a concise route with a stereoconvergent intramolecular Diels-Alder reaction. The key step involved a Nozaki-Hiyama-Kishi reaction to connect the enone system and diene, followed by a stereoconvergent IMDA reaction to furnish the natural product carboskeleton in 7 steps. The reactions were carried out successfully on a gram scale up to an advanced intermediate, including the stereoconvergent intramolecular Diels-Alder reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A Yb(OTf)(3)-catalyzed formal (4 + 3) cycloaddition reaction was successfully achieved using donor-acceptor cyclopropanes and 3-benzylideneindoline-2-thiones as reactants. Functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. This reaction represents the first (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qun Zhao, Yao Li, Qing-Xia Zhang, Jin-Pei Cheng, Xin Li
Summary: The highly enantioselective aza-Diels-Alder reaction of 2-aryl-3H-indol-3-ones with unactivated dienes using a B(C6F5)(3)/chiral phosphoric acid catalyst system under mild conditions offers rapid access to a broad scope of tetrahydropyridine derivatives with excellent outcomes. The reaction is efficient, with maintained enantioselectivity even at lower catalyst loadings of 0.1 mol %. DFT calculations provide convincing evidence for the interpretation of stereoselection.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Chin-Hung Lai, Cheng-En Yang, Yang-Chang Wu, Youness El Bakri, Eduardo Chamorro, Ta-Hsien Chuang
Summary: In this study, we explained why the substitution of a cyano group onto the 1-azadiene moiety promotes an intramolecular aza-Diels-Alder reaction, and found that this reaction has an inverse electron demand.
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Applied
Maxim G. Vinogradov, Olga V. Turova, Sergei G. Zlotin
Summary: This review retrospectively considers the pivotal achievements and recent advances in catalytic asymmetric aza-DAR reported up to 2020, showcasing their potency for enantioselective synthesis of useful chiral piperidine, quinoline, pyridazine, oxazine, and oxadiazine derivatives. The data are systematized based on key electron transfer modes and attainable heterocyclic products, with significant attention to activation strategies and plausible reaction pathways over stereoselective cyclization processes. The review contains 310 references and 122 synthetic schemes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Aurapat Ngamnithiporn, Padon Chuentragool, Poonsakdi Ploypradith, Somsak Ruchirawat
Summary: This article reports the development of a novel three-component aza-Diels-Alder reaction, employing sultines, aldehydes, and amines as substrates. By using Cu(OTf)(2) as a Lewis acid catalyst and the in situ generation of imines, a wide range of polysubstituted tetrahydro-isoquinoline derivatives can be easily prepared from readily available precursors. The synthetic utility of these products is demonstrated through various product transformations, including the synthesis of tricyclic N-heterocycles.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Angelica Penaranda Gomez, Carlos E. Puerto Galvis, Mario A. Macias, Cristian Ochoa-Puentes, Vladimir V. Kouznetsov
Summary: A novel tandem approach was developed for the efficient synthesis of substituted chromeno[4,3-b]quinolines under metal-catalyst-and photosensitizer-free reaction conditions. The method, based on an inexpensive I(2)/DMSO system, features mild conditions, high step-economy, and provides a new access to biologically important nitrogen- and oxygen-containing heterocyclic molecules.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Wei-Ling Jiang, Bin Huang, Meng-Xiang Wu, Ye-Kai Zhu, Xiao-Li Zhao, Xueliang Shi, Hai-Bo Yang
Summary: The preparation of stable MOFs with organic radicals is challenging due to the reactivity of most organic radicals. A novel MOF containing phenazine radical cations was successfully synthesized using a post-synthetic modification strategy. The resulting MOF demonstrated high catalytic activity in aza-Diels-Alder reactions and excellent stability and recyclability, suggesting the potential of the developed strategy for preparing radical-based MOFs for heterogeneous catalysis in organic synthesis.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Yi-Min Fan, Josemon George, Jiao Yu J. Wang, Michael G. Gardiner, Michelle L. Coote, Michael S. Sherburn
Summary: Through the study, it was found that imines can participate in intermolecular formal [4 + 2] cycloadditions with dendralenes, forming hexahydro- and octahydro-isoquinoline structures. After optimizing the conditions, the formal aza-Diels-Alder reaction proceeds with high regio- and stereoselectivity.
Review
Biochemistry & Molecular Biology
Malika Ibrahim-Ouali
Article
Materials Science, Multidisciplinary
Marc Lepeltier, Bernadette Graff, Jacques Lalevee, Guillaume Wantz, Malika Ibrahim-Ouali, Didier Gigmes, Frederic Dumur
ORGANIC ELECTRONICS
(2016)
Review
Chemistry, Organic
Thanh-Tuan Bui, Fabrice Goubard, Malika Ibrahim-Ouali, Didier Gigmes, Frederic Dumur
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Assi Al Mousawi, Ahmad Arar, Malika Ibrahim-Ouali, Sylvain Duval, Frederic Dumur, Patxi Garra, Joumana Toufaily, Tayssir Hamieh, Bernadette Graff, Didier Gigmes, Jean-Pierre Fouassier, Jacques Lalevee
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2018)
Article
Chemistry, Multidisciplinary
Frederic Dumur, Malika Ibrahim-Ouali, Didier Gigmes
APPLIED SCIENCES-BASEL
(2018)
Review
Chemistry, Multidisciplinary
Thanh-Tuan Bui, Fabrice Goubard, Malika Ibrahim-Ouali, Didier Gigmes, Frederic Dumur
APPLIED SCIENCES-BASEL
(2018)
Review
Biochemistry & Molecular Biology
Malika Ibrahim-Ouali, Frederic Dumur
Article
Chemistry, Physical
Aude-Heloise Bonardi, Soraya Zahouily, Celine Dietlin, Bernadette Graff, Fabrice Morlet-Savary, Malika Ibrahim-Ouali, Didier Gigmes, Norbert Hoffmann, Frederic Dumur, Jacques Lalevee
Article
Materials Science, Multidisciplinary
Aude-Heloise Bonardi, Soraya Zahouily, Celine Dietlin, Bernadette Graff, Frederic Dumur, Malika Ibrahim-Ouali, Didier Gigmes, Jacques Lalevee
Review
Polymer Science
Nicolas Giacoletto, Malika Ibrahim-Ouali, Frederic Dumur
Summary: The development of photoinitiating systems activable in the visible and near-infrared region is an active research field, with squaraine dyes serving as relevant examples that offer various absorption wavelengths to revolutionize the scope of photopolymerization applications.
EUROPEAN POLYMER JOURNAL
(2021)
Article
Polymer Science
Malika Ibrahim-Ouali, Frederic Dumur
Summary: Photopolymerization is undergoing a revolution with the availability of cheap, lightweight, compact, and energy-saving light sources like LEDs. Research is actively seeking photoinitiating systems that can be activated under low light intensity in the visible range and exhibit high reactivity even under air, with chalcones being a promising candidate fitting these requirements. Recent developments in chalcone-based photoinitiating systems are discussed in this review, highlighting their crucial importance through comparisons with benchmark photoinitiators.
EUROPEAN POLYMER JOURNAL
(2021)
Article
Chemistry, Organic
Besma Bendif, Nadjia Bensouilah, Frederic Dumur, Malika Ibrahim-Ouali
Summary: Thiazinones containing sulfonamides, key in new pharmaceutical molecule design, are synthesized efficiently from commercially available compounds and their structures are established by X-ray crystallography. Biological activity of these compounds is currently under evaluation.
Article
Chemistry, Organic
Malika Ibrahim-Ouali, Frederic Dumur
Review
Chemistry, Organic
Malika Ibrahim-Ouali, Frederic Dumur
Review
Chemistry, Organic
Malika Ibrahim-Ouali, Frederic Dumur
Article
Chemistry, Organic
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.
Article
Chemistry, Organic
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.
Article
Chemistry, Organic
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.
