Article
Chemistry, Organic
Jiao-Jiao Han, Tao Jiang, Cui Zhang, Dan-Dan Cui, Yuan-Zhao Hua, Guang-Jian Mei, Min-Can Wang, Shi-Kun Jia
Summary: The enantioselective [3 + 2] annulation of α-hydroxy-1-indanones with yne-enones was achieved using dinuclear zinc catalysts via a Bronsted base and Lewis acid cooperative activation model. A variety of enantioenriched spiro[2,3-dihydrofuran-2,2'-inden-1-one] derivatives were obtained with high yields, excellent diastereoselectivities, and enantiostereoselectivities (up to 84% yield, 20:1 dr, 99% ee). This method offers a broad substrate scope, gram-scale synthesis, and late-stage functionalization of complex molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Emily E. Freeman, Randy Jackson, Jessica Luo, Rajen Somwaru, Alex A. Sons, Andrew Bean, Ronald N. Buckle, R. Jason Herr
Summary: We present a versatile method for the synthesis of N-substituted 3,4-dihydroisoquinolin-1(2H)-one compounds through a three-step sequence of cross-coupling, cyclization, N-deprotection, and N-alkylation. Mechanistic studies were conducted to understand the order of transformations in the cyclization and N-alkylation processes. This method was also applied to the synthesis of N-benzyl isoindolin-1-one and N-benzyl 2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Ekaterina E. Khramtsova, Ekaterina A. Lystsova, Evgeniya V. Khokhlova, Maksim V. Dmitriev, Andrey N. Maslivets
Summary: The 3-hydroxy-1,5-dihydro-2H-pyrrol-2-one motif is valuable in drug discovery, and replacing the 3-oxy fragment with a 3-amino one can significantly impact the biological effect of compounds. Developing approaches to 3-amino-1,5-dihydro-2H-pyrrol-2-ones is of significant interest, and a new approach involving thermal decomposition of urea derivatives was successfully developed in this study.
Article
Chemistry, Applied
Ajay H. Bansode, Gurunath Suryavanshi
Summary: The controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines using visible light-rose bengal-TBHP mediation has been developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. This method shows a broad substrate scope, good functional group tolerances, and the products are obtained in good to excellent yields. Additionally, the methodology has been successfully applied in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one, a topoisomerase-I inhibitor.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Suven Das, Arpita Dutta
Summary: This review focuses on recent advancements in the cyclization reactions of 1-indanones, specifically on the construction of fused- and spirocyclic frameworks. New synthetic strategies for the synthesis of various carbocyclic and heterocyclic skeletons are demonstrated. The review also highlights the formation of biologically relevant compounds and natural products.
Article
Chemistry, Multidisciplinary
Zhi-Lin Wu, Jin-Yang Chen, Xian-Zhi Tian, Wen-Tao Ouyang, Zhuo-Tao Zhang, Wei-Min He
Summary: A novel and efficient electro-chemical initiated radical strategy was developed for the preparation of both N-substituted and N-unsubstituted 4-selanylisoquinolin-1(2H)-ones through selenylation of isoquinolin-1(2H)-ones with organodiselenides under chemical oxidant-, additive-free and ambient conditions.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Xiao-Hong Huang, Cai-Yun Yang, Feng-Lin Liu, Xia Li, Bo Liu, Jun-Feng Kou, Guo-Li Huang, Ming-Yu Teng
Summary: A novel three-component Pd/norbornene cooperative catalysis cascade decarboxylative [2+2+2]/[2+2+3] cyclization has been developed for the synthesis of fused phenanthridinones and hepta[1,2-c]isoquinolinones. The method demonstrates unique regioselectivity and broad substrate scope, utilizing Pd/NBE-catalyzed C-H activation and subsequent decarboxylative coupling reactions, where NBE serves as a building block for constructing rigid nonplanar molecular architectures.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yangxiu Mu, Minghua Yang, Fengxia Li, Zafar Iqbal, Rui Jiang, Jing Hou, Xin Guo, Zhixiang Yang, Dong Tang
Summary: An efficient sulfuration of isoquinolin-1(2H)-ones at the C-4 position has been reported using ethyl sulfinates and iodine, resulting in moderate to excellent yields of thioether-isoquinolin-1(2H)-ones. The method is also applicable to pyridin-2(1H)-one, providing the corresponding thioether product in moderate yield, with a plausible mechanism suggested based on preliminary mechanistic studies.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Applied
Zhen Yao, Ji Yang, Zhenli Luo, Jianhan Ye, Jiahong Han, Xin Zhang, Lijin Xu, Peng Wang, Qian Shi
Summary: This study presents a tandem one-pot regioselective synthesis method under visible-light photocatalysis, providing a straightforward approach for the synthesis of C4-difluoroalkylated phthalazin-1(2H)-ones with broad substrate scope and wide functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
You-Quan Zhu, Li-Wen Hui, Shi-Bo Zhang
Summary: A Palladium(0)-catalyzed C4 site-selective C-H difluoroalkylation of isoquinolin-1(2H)-ones was reported for the first time, allowing for the efficient installation of difluoroacetate or difluoroacetamide moieties into bioactive molecules. Introduction of difluorinated groups at the C4 position was shown to enhance the antiviral activity of the compounds, with compound 5ab exhibiting similar antiviral activity to commercial Ningnanmycin.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Sudip Shit, Bipin Kumar Behera, Subhamoy Biswas, Anil K. K. Saikia
Summary: A metal-free Lewis acid-initiated protocol has been developed for the synthesis of highly substituted 3-(dihydrofuran-3(2H)-ylidene)isobenzofuran-1(3H)-imines. The reaction involves the formation of dihydrofuranylidene carbocation followed by intramolecular cyclization, leading to the desired products in moderate to good yields. The methodology can also be extended to the synthesis of 3-(dihydro-2H-pyran-3(4H)-ylidene)-isobenzofuran-1(3H)-imines, and furanylidene isobenzofuranones can be obtained in excellent yields through post synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Debabrata Barman, Tanmoy Ghosh, Krishanu Show, Sudipto Debnath, Tapas Ghosh, Dilip K. Maiti
Summary: The N-heterocyclic carbene-catalyzed tandem Stetter-aldol reactions of phthalaldehyde and alpha,beta-unsaturated ketimines yielded functionalized naphthalen-1(2H)-one derivatives as [4+2] annulation products, while the reactions of aldimines resulted in the formation of isoquinoline derivatives instead of the expected indanone derivatives as [4+1] annulation products, showcasing a novel synthetic strategy.
Article
Chemistry, Organic
Yuan-Xiang He, Kui Hu, Yu Ran, Zhen-Yao Lei, Shu Geng, Li-Na Chen, Li Pan, Jun-Bo Zhong, Feng Huang
Summary: This study presents a novel method for the one-pot construction of structurally new isoindolinone and isoquinolinone fused oxazinane compounds through intramolecular cascade cyclization using photogenerated N-amidyl radicals. The transformation proceeds smoothly under mild conditions, with low catalyst loading and good functional group tolerance, providing an efficient and concise approach for synthesizing valuable nitrogen-containing polyheterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Leticia B. Silva, Felipe S. Stefanello, Sarah C. Feitosa, Clarissa P. Frizzo, Marcos A. P. Martins, Nilo Zanatta, Bernardo A. Iglesias, Helio G. Bonacorso
Summary: This paper covers the synthesis of a series of new 7-(1H-pyrrol-1-yl)spiro[chromeno[4,3-b]quinoline-6,1 '-cycloalkanes] and their application in traditional CC and CN cross-coupling reactions. The synthesized compounds showed high emission properties, good phi(f) values, and moderate to large Stokes shifts.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Cai-Yun Yang, Lin-Ping Hu, De-Run Zhang, Xia Li, Ming-Yu Teng, Bo Liu, Guo-Li Huang
Summary: A general and efficient procedure for the iodination of isoquinolin-1(2H)-ones using N-iodosuccinimide under the catalysis of p-toluenesulfonic acid at room temperature is presented. This method offers an alternative approach for the formation of C-I bonds, resulting in the synthesis of various 4-iodoisoquinolin-1(2H)-ones in moderate to good yields. The procedure demonstrates a wide substrate scope and excellent tolerance towards functional groups.
NEW JOURNAL OF CHEMISTRY
(2022)
