Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yifei Qu, Xiaojia Cai, Yuzhuang Guan, Jiamin Tan, Zhangping Cai, Minyun Liu, Yasi Huang, Jinhui Hu, Wen-Hua Chen, Jia-Qiang Wu
Summary: A facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes, and indole-3-methanamines by a Friedel-Crafts reaction is developed, showing good to excellent yields, broad substrate compatibility, good functional group tolerance, and scalability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ning Li, Wenjing Lu, Weizhi Gu, Kuiliang Li, Jindong Li, Yangmian Lu, Zhenggen Zha, Zhiyong Wang
Summary: An asymmetric Michael/hemiketalization reaction was developed between isatin-derived beta, gamma-unsaturated alpha-ketoesters and 4-hydroxycoumarins in aqueous media. A series of chiral spirooxindole derivatives with an all-carbon quaternary stereogenic center were obtained in high yields (up to 93%) and excellent enantioselectivities (up to 98%).
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Pan Tang, You -Yuan Wei, Long Wen, Hao-Jie Ma, Yi Yang, Yan Jiang
Summary: This article investigates the MgI2-catalyzed nucleophilic ring-opening reactions of donor-acceptor cyclopropanes with indoline-2-thiones as sulfur nucleophiles. Under mild reaction conditions, a series of functionalized gamma-indolylthio butyric acid derivatives are obtained in good to excellent yields. Additionally, the thioether functionalized ring-opening products can be transformed into sulfone and methionine analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dong-Chao Wang, Pan-Pan Wu, Pei-Yu Du, Gui-Rong Qu, Hai-Ming Guo
Summary: A palladium-catalyzed domino Heck/decarboxylative alkynylation reaction has been developed for the synthesis of 3,3-disubstituted oxindoles and hydropyrimidinyl spirooxindoles from trisubstituted alkenes or enamines. The reaction showed good yields and demonstrated its wide applicability through gram-scale syntheses and diverse transformations of the reaction products. The enantioselective version of the reaction was also investigated.
Article
Chemistry, Organic
Cheng Huang, Zhifei Zhao, Shiwu Li, Jixing Zhao, Leifang Wu, Chengzhi Gu
Summary: A highly enantioselective conjugate addition has been developed for the reaction between indolizine and its analogues with alpha,beta-unsaturated 2-acyl imidazoles. This method provides excellent yields and enantioselectivities, overcoming the limitations of organocatalysts in controlling stereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Juan J. Rojas, Elena Torrisi, Maryne A. J. Dubois, Riashat Hossain, Andrew J. P. White, Giovanni Zappia, James J. Mousseau, Chulho Choi, James A. Bull
Summary: This paper reports a method for synthesizing 1,4-dioxanes and explores the catalytic mechanism of the reaction. The reaction exhibits high regio- and diastereoselectivity, and the resulting products serve as interesting motifs for drug discovery.
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Organic
Velu Saravanan, Arasambattu K. Mohanakrishnan
Summary: A one-pot synthesis of aryl- and heteroaryl-annulated carbazoles was achieved from 2/3-bromomethylindoles, along with a bis-domino reaction of 2,5-bis(bromomethyl)pyrrole with selected heteroarenes. The synthesized thienocarbazoles and thienodibenzofurans were successfully utilized for a second-generation domino reaction.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Jia-Qi Wu, Xin-Yuan Wu, Jian-Mei Lu, Qian Shi, Li-Xiong Shao
Summary: In this study, a novel La(III)-based two-dimensional metal-organic framework was synthesized and used as an efficient Lewis acid catalyst for the Friedel-Crafts alkylation reaction. The catalyst exhibited a unique structure, good stability and catalytic activity in acidic and basic environments.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Nicolas Zeidan, Sergiu Bicic, Robert J. Mayer, David Leboeuf, Joseph Moran
Summary: This study demonstrates that HFIP greatly expands the scope of the Bronsted acid-catalyzed hydroarylation of enamides, and acts as a slow-release reservoir for the key cationic intermediate. The reaction is fast and practical, and can prevent the oligomerization of the substrate.
Article
Chemistry, Organic
Duc Chu, Jonathan A. A. Ellman
Summary: Unprotected, alpha,beta-disubstitutedtryptaminesand phenethylamines can be obtained through a one-pot, metal-free sequence involving in situ formation of aziridinium salts and subsequent Friedel-Crafts reaction with electron-rich (hetero)-arenes. The use of hexafluoroisopropanol as the solvent greatly facilitates both steps. This method is effective for variously substituted indoles and 1,3,5-trimethoxybenzene, as well as cyclic and acyclic alkenes, exhibiting stereospecificity for both (E)- and (Z)-1,2-disubstituted alkenes. Additionally, a diamine can be synthesized via one-pot morpholine addition to an aziridinium salt.
Article
Chemistry, Applied
Yanshun Li, Mengqi Dong, Nanxing Gao, Guorui Cao, Dawei Teng
Summary: A zinc complex of a new spiroQuinox ligand with a spirocarbon stereogenic center was used for asymmetric Friedel-Crafts alkylation of indoles with cyclic N-sulfonyl ketimino esters. This catalytic system allows for facile synthesis of benzosultam derivatives functionalized with indole substituents, with high yield and excellent enantioselectivity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Fang Lv, Jing Xiao, Junchun Xiang, Fengzhe Guo, Zi-Long Tang, Li-Biao Han
Summary: For the first time, H3PO3 was utilized as both the reducing reagent and the promotor in reductive benzylation reactions with aryl aldehydes. The combination of H3PO3/I-2 enabled various aromatic aldehydes to undergo iodination reactions and Friedel-Crafts type reactions with arenes, easily producing benzyl iodides and diarylmethanes in good yields while also leading to intramolecular cyclization reactions to give corresponding cyclic compounds. This novel strategy offers advantages of easy-handling, low-cost, and metal-free conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
