Article
Chemistry, Organic
Yang Liu, Mikael La Roch, Alessia Mori, Alexandre Pradal, Giovanni Poli, Julie Oble
Summary: The article introduces a Pd(II)-catalyzed [3+2] annulation strategy, which replaces α,β-unsaturated-γ-oxy carbonyls with β,γ-unsaturated carbonyl derivatives as bis-electrophiles. The study provides experimental optimization and demonstrates the synthetic versatility in forming diverse heterocyclic structures. This dehydrogenative strategy represents a more economical version than the previous redox-neutral couplings.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jin Xi, Ding Wang, Jinxia Hu, Huan Shen, Tao Wang, Zunting Zhang
Summary: A method for synthesizing benzo[f]quinoline derivatives via photoinduced 6 pi-electrocyclization has been developed. The reaction conditions are mild, and the yields are high without the need for transition metal catalysts or additives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Jin Xi, Ding Wang, Jinxia Hu, Huan Shen, Tao Wang, Zunting Zhang
Summary: A method for the synthesis of trans-dihydrobenzo[f]quinolines 2, cis-dihydrobenzo[f]quinolines 3 and 8b-methyl-1,8b-dihydrobenzo[f]quinolines 4 was developed by photoinduced 6p-electrocyclization of 2-(benzofuran-2-yl)-3-phenylpyridine derivatives 1. Irradiation of 2-(benzofuran-2-yl)-3-phenylpyridine 1 in acetone-H2O (5 : 1, v/v) with a 313 nm UV lamp yielded 2, which was further converted into 3 at elevated temperature in glycerol. Irradiating 2-(3-methylbenzofuran-2-yl)-3-phenylpyridines 1 in CH2Cl2 with a 254 nm UV lamp gave 4 in good yields. The syntheses of 2, 3 and 4via the 6p-electrocyclization rearrangement of 1 offer high atom efficiency and do not require transition metal catalysts or additives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Shrikant M. Khake, Naoto Chatani
Summary: The Rh(III)-catalyzed reaction of aniline derivatives containing a pyrimidine directing group with vinylsilanes leads to the formation of C3-substituted indoline derivatives via a highly regioselective C-H activation/alkene cyclization cascade. Mechanistic experiments suggest that C-H bond cleavage is not the rate-determining step, but rather the reaction proceeds through the formation of a six-membered rhodacycle as a key catalytic species via pyrimidine-directed electrophilic ortho-C-H rhodation.
Article
Chemistry, Organic
Jin-xin Zhu, Jin-Miao Tian, Yao-Yao Chen, Xue-Jiao Hu, Xue Han, Wenchao Chen, Zhikun Yang, Xiaoze Bao, Xinyi Ye, Hua Chen, Fu-Min Zhang, Hong Wang, Yong-Qiang Tu
Summary: An asymmetric [3+2] cycloaddition reaction between quinone esters and 2,3-dihydrofuran has been successfully achieved using a newly developed Cu(II)/SPDO complex. This reaction provides a straightforward route for the synthesis of 2,3,3a,8a-tetrahydrofuro[2,3-b]benzofurans with high enantioselectivity and diastereoselectivity. The resulting compounds contain two adjacent stereocenters and a continuously functionalized benzene ring. The reaction can be easily scaled up and used for the expedient synthesis of specific natural compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hong Ji, Juan Zou, Chengli Mou, Yonggui Liu, Shi-Chao Ren, Yonggui Robin Chi
Summary: In this study, a N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition was developed to rapidly construct complex molecules with a tricyclic core and morpholine moiety. The success of the reaction relied on the NHC-catalyzed remote sp(3) (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies demonstrated that the products showed superior in vitro bioactivities against two plant pathogens compared to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC).
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Daria V. Vorobyeva, Dmitry A. Petropavlovskikh, Ivan A. Godovikov, Fedor M. Dolgushin, Sergey N. Osipov
Summary: A convenient method has been developed for the synthesis of a new series of alpha-CF3-substituted alpha-amino acid derivatives bearing pharmacophore isoquinolone core. The method involves the [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing alpha-amino carboxylates under Rh(III)-catalysis. The resulting annulation products can be easily transformed into valuable isoquinoline derivatives through a successive aromatization/cross-coupling operation.
Article
Chemistry, Organic
Teng Liu, Yuqi Fang, Linhong Zuo, Yulian Yang, Yin Liu, Weipeng Chen, Li Dang, Wusheng Guo
Summary: A practical and straightforward methodology for synthesizing non-fused N-aryl azepane derivatives with diversity has been described. The reactions proceed smoothly under mild conditions with CO2 as a byproduct, and the resulting products can be easily converted into a range of highly functionalized azepanes. The DFT calculations reveal the details of the reaction pathway and the origin of the unusual exclusive [5 + 2] annulation process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Feroz Ahmad, Pavit K. Ranga, Shaheen Fatma, Arun Kumar, Ramasamy Vijaya Anand
Summary: This article describes an effective and economical method for synthesizing various important functionalized indolizine derivatives. This transformation is achieved through a Cu(II)-catalyzed [3+2] annulation of 2-pyridinyl substituted p-quinone methides with enaminones. The method has good functional group tolerance and is effective for most enaminones and p-QMs, resulting in moderate to good yields of indolizines.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Manoj Kumar, Shalini Verma, Vivek Mishra, Oliver Reiser, Akhilesh K. Verma
Summary: The copper-catalyzed reactions under visible light irradiation have been successfully applied in the synthesis of aminated cyclopentene and cyclopentane derivatives. The method is compatible with various functionalities and demonstrates simplicity and affordability.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Xun Tian, Ailin Pan, Ya Du, Lening Zhang, Cuirong Qin, Shengzu Duan, Lijuan Yang, Xiaodong Yang
Summary: This paper describes an approach for the synthesis of 2-acyl indolines through Cobalt-catalyzed C-H activation/[3+2] annulation of aniline derivatives and acrylates. The method utilizes a cobalt catalyst to achieve high regioselectivity in the formation of functionalized 2-acylindolines. The mechanism is investigated through KIE experiments and deuterium-labeling experiment. The scalability and application value of the method is confirmed through gram-scale synthesis and synthetic transformations.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Dawn H. White, Adam Noble, Kevin Booker-Milburn, Varinder K. Aggarwal
Summary: The reaction described is a highly diastereoselective visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins, leading to the construction of trans-cyclopentanes with synthetically useful functional groups. This reaction proceeds via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical and subsequent 5-exo cyclization.
Article
Chemistry, Multidisciplinary
Arnab Dey, Anurag Singh, Chandra M. R. Volla
Summary: The efficient oxidative [3 + 2] annulation reaction of aryl hydrazones and heterobicyclic alkenes has been achieved using inexpensive cobalt salts under aerobic conditions. The reaction generates complex indane derivatives with high anti-diastereoselectivity, avoiding the use of stoichiometric amounts of metal oxidants.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Zhipeng Guan, Shuxiang Zhu, Yayu Ye, Xiangwei Li, Yanlong Liu, Pengjie Wang, Heng Zhang, Zhiliang Huang, Aiwen Lei
Summary: In this study, an electrochemical mediator-induced intermolecular selective (3+2) annulation was developed for the synthesis of a library of decorated cyclopentenes and cyclopentanes. This method offers high efficiency, mild reaction conditions, broad substrate scope, good functional group tolerance, and high regioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Farrukh Sajjad, Alavala Gopi Krishna Reddy, Dong Xing, Suzhen Dong, Wenhao Hu
Summary: An unprecedented synthetic route towards a variety of 3-anilino-1H-indoles has been achieved through a domino ruthenium-catalyzed annulation and subsequent iron-promoted fragmentation and rearrangement. The strategy is applicable to deliver diversely substituted indole esters, with compound 4i exhibiting the best inhibitory activity with an IC50 value of 0.05 mu M, paving the way for the discovery of promising lead compounds in the future.