Article
Chemistry, Applied
Dario Allegue, Javier Santamaria, Alfredo Ballesteros
Summary: In this study, a gold(I)-catalyzed and atom-economical synthesis of ortho-N-indolyl-N-pyrazolylbenzene from 1,2,3-triazapentalenes and ynamides was reported. The reaction involves the cleavage of the triazole ring, formation of an alpha-imino gold carbene intermediate, and an aza-Nazarov-type cyclization with participation of an arene ring. The formal [4+1] heterocycloaddition reaction provides the four-carbon synthon from the ynamide, and indole synthesis can also be achieved in a one-pot procedure from their 1-propargyl-1H-benzotrizaole precursors.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Wei Wu, Beibei Luo, Yi You, Zhiqiang Weng
Summary: A novel synthesis approach for the construction of 2-trifluoroethyl-substituted benzofurans under copper-catalyzed conditions has been developed, with moderate to excellent yields (up to 93%). This method is also applicable to the formation of 2-trifluoroethylated indoles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Luca C. C. Greiner, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Summary: In this study, phenyl azides substituted by an (alkylphenyl)ethynyl group were found to facilitate benzylic sp(3)(C-H) functionalization under the presence of a JohnPhosAu catalyst, resulting in the synthesis of indole-fused tetra- and pentacycles through divergent N- or C-cyclization. The chemoselectivity of the reaction was found to be influenced by the counter-anion, the electron density of the alpha-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Zixuan Tong, Olivia L. Garry, Philip J. Smith, Yubo Jiang, Steven J. Mansfield, Edward A. Anderson
Summary: This study reports a gold-catalyzed oxidative functionalization reaction to access unnatural amino acid derivatives using a wide range of nucleophiles. The reaction proceeds under mild conditions with high functional group tolerance, and displays excellent regioselectivity through subtle steric differentiation of the yndiamide nitrogen atom substituents.
Article
Chemistry, Organic
Manjunath S. Lokolkar, Pravin A. Mane, Sandip Dey, Bhalchandra M. Bhanage
Summary: An effective method for synthesizing 2-substituted indoles through addition/reductive cyclization in a one-pot tandem reaction has been presented. This method tolerates a wide range of functional groups and provides moderate to good yields. The gram-scale synthesis of 2-substituted indole has also been demonstrated. This protocol offers an alternative route for the synthesis of 2-substituted indoles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ali Osman Karatavuk
Summary: A highly efficient method for the synthesis of 2-pyridonyl alcohols via a gold(i) catalyst and methanesulfonic acid has been developed. The proposed mechanism involves intramolecular cyclization product formation, leading to the formation of N-alkenyl pyridonyl alcohols in moderate to excellent yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Hongmei Zhu, Lei Chen, Rongxian Bai, Yanlong Gu
Summary: Two classes of indole-tetrahydropyridine hybrid molecules were synthesized via three-component reactions, providing a straightforward approach for accessing diverse molecular structures. The reactions were likely triggered by Michael addition, leading to the formation of indol-3-ylimine intermediate, which was then trapped by the indole component. The resulting indol-3-yl-substituted tetrahydropyridines could be converted into indole-pyridine hybrid molecules with the aid of DDQ.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Baofu Zhu, Jiaming He, Kai Zou, Anquan Li, Chen Zhang, Jiaji Zhao, Hua Cao
Summary: This study established a three-component reaction catalyzed by base, involving ynals, isocyanates, amines, and alcohols. The strategy enables a wide range of substrates and provides a simple process for the preparation of diverse pyridine derivatives with good yields and high regioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tao Cai, Chengjie Feng, Fangqi Shen, Kejun Bian, Chunlei Wu, Runpu Shen, Yuzhen Gao
Summary: An Ag-catalyzed cyclization/demethylation reaction is described for the synthesis of valuable benzothio(seleno)phenes and indoles under mild conditions with low catalyst loading, resulting in good to excellent yields of various 2-substituted benzothio(seleno)phenes and indoles. The method is exemplified with a concise synthesis of a bioactive molecule precursor, and a possible reaction mechanism is proposed based on isotope-exchange experiments.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Stefano Nejrotti, Francesco Marra, Emanuele Priola, Andrea Maranzana, Cristina Prandi
Summary: The reactivity of furan-ynes in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, affording functionalized dihydropyridinones and pyranones.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Guanghui Wang, Jian Jia, Gang Liu, Mingwu Yu, Xiaoxiao Chu, Xiguang Liu, Ximei Zhao
Summary: An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction has been developed, providing a practical tool for synthetic and pharmaceutical chemists. The method avoids multi-step operation and the use of highly toxic cyanides, with various products obtained with perfect regioselectivity in moderate to good yields. The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Ke-Fan Wu, Dong-Ting Dai, Xin-Yue Sun, Yun-He Xu
Summary: A copper-catalyzed borylation of propargyl dichlorides was developed, leading to the formation of chloro-substituted allenyl-Bdan products in good yields under mild reaction conditions. The utilities of these products were examined through various derivatizations.
Article
Chemistry, Organic
Dan-Bi Sung, Jong Seok Lee
Summary: This study describes a gold(I)-catalyzed intermolecular formal [2 + 2 + 2] cycloaddition reaction, which selectively synthesizes highly substituted 2H-pyrans using different metal triflate additives. This method provides a new opportunity for the synthesis of other heterocyclic compounds.
Article
Chemistry, Multidisciplinary
Riccardo Pedrazzani, Emanuele Pinosa, Giulio Bertuzzi, Magda Monari, Samuel Lauzon, Thierry Ollevier, Marco Bandini
Summary: A new Au(i) catalyzed intramolecular hydrocarboxylation of allenes is presented, which serves as a valuable synthetic route to oxazino-indolones. The use of 3,5-(CF3)(2)-C6H3-ImPyAuSbF(6) as the optimal catalyst allows for wide tolerance of functional groups, mild reaction conditions, and high yields. Preliminary attempts towards an enantioselective version are also documented using a new family of chiral C-1-symmetric ImPyAuCl complexes.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Weiping Zhou, Arnaud Voituriez
Summary: An efficient and straightforward gold-catalyzed protocol has been developed for the synthesis of 2-substituted 4-oxo-4-arylbutanal derivatives, allowing for the facile synthesis of cycloalkyl-1-one compounds of different ring sizes. The methodology was also extended to the synthesis of tetrahydrocycloalkyl[b]pyrrole derivatives found in active pharmaceutical ingredients, with a mechanistic investigation revealing a [3,3]-sigmatropic rearrangement of a sulfonium intermediate in the process.
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)