35295-60-4Relevant articles and documents
Visible-light-promoted catalyst-/additive-free synthesis of aroylated heterocycles in a sustainable solvent
Zeng, Fan-Lin,Xie, Kun-Chen,Liu, Yu-Ting,Wang, He,Yin, Peng-Cheng,Qu, Ling-Bo,Chen, Xiao-Lan,Yu, Bing
, p. 1732 - 1737 (2022/03/07)
A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocycles (55 examples, up to 95% yield, including modification of pharmaceuticals and natural products) such as thioflavones, benzimidazo[2,1-a]isoquinolin-6(5H)-ones, indolo[2,1-a]isoquinolin-6(5H)ones, quaternary 3,3-dialkyl 2-oxindoles, quinoxalin-2(1H)-ones, and benzo[e][1,2,3]oxathiazine 2,2-dioxides in a green solvent (dimethyl carbonate) under air and room temperature conditions. This practical acylation process was achieved using 4-acyl-1,4-dihydropyridines (acyl-DHPs) as acylating reagents under mild conditions, avoiding the use of catalysts, bases, additional oxidants, and traditional organic solvents. This journal is
Photoredox Catalyzed Radical Cascade Aroylation (Sulfonylation)/Cyclization Enables Access to Fused Indolo-pyridones
Yang, De-Yong,Liu, Liang,Gu, Jia-Yi,He, Yan-Hong,Guan, Zhi
, p. 18042 - 18055 (2021/12/17)
A visible-light-initiated radical cascade reaction toward the synthesis of structurally diverse fused Indolo-pyridones is described. The reaction involves the addition of aroyl or sulfonyl radicals to N-alkyl-acryloyl-1H-indole-3-carboxamides, cyclization, and oxidative aromatization. This telescoped method circumvents lengthy prefunctionalization steps of radical precursors, which is further underpinned by the superior compatibility with a series of C-centered radicals, allowing the rapid and facile construction of numerous valuable architectures.
The visible-light-induced acylation/cyclization of alkynoates with acyl oximes for the construction of 3-acylcoumarins
Chen, Pu,Liu, Yu,Tang, Ke-Wen,Xiong, Bi-Quan,Xiong, Fang-Ting,Zhou, Quan
supporting information, p. 9012 - 9020 (2021/11/04)
A nitrogen-centered radical-mediated carbon-carbon bond cleavage strategy is described to synthesize functionalized 3-acylcoumarins. The strategy is enabled by the visible-light-induced acylation/cyclization of alkynoates with various acyl oxime compounds in acetonitrile. The difunctionalization of carbon-carbon triple bonds precedes the generation of iminyl radicals, which is followed by the formation of acyl radicals. The acyl radicals then attack the carbon-carbon triple bonds, followed by 5-exo-trigcyclization and 1,2-ester migration. This strategy has wide substrate adaptability and good substituent tolerance.
Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines
Luo, Xiaosheng,Wang, Ping
supporting information, p. 4960 - 4965 (2021/07/20)
Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.
Copper-catalyzed coupling of anthranils and α-keto acids: Direct synthesis of α-ketoamides
Li, Ping-Gui,Zhu, Hao,Fan, Min,Yan, Cheng,Shi, Kai,Chi, Xi-Wen,Zou, Liang-Hua
supporting information, p. 5902 - 5907 (2019/06/24)
Copper-catalyzed coupling of α-keto acids with anthranils is reported for the synthesis of α-ketoamides. This process involves N-O/C-O bond cleavages and C-N bond formation. Furthermore, the decarboxylation of α-keto acids can be successfully suppressed under redox-neutral conditions.
Visible Light-Induced Decarboxylative Acylarylation of Phenyl Propiolates with α-Oxocarboxylic Acids to Coumarins Catalyzed by Hypervalent Iodine Reagents under Transition Metal-Free Conditions
Yang, Shuai,Tan, Hui,Ji, Wangqin,Zhang, Xiangbiao,Li, Pinhua,Wang, Lei
supporting information, p. 443 - 453 (2017/02/10)
No Abstract. (Figure presented.).
Sunlight-Driven Decarboxylative Alkynylation of α-Keto Acids with Bromoacetylenes by Hypervalent Iodine Reagent Catalysis: A Facile Approach to Ynones
Tan, Hui,Li, Hongji,Ji, Wangqin,Wang, Lei
supporting information, p. 8374 - 8377 (2015/11/27)
A novel and practical decarboxylative alkynylation of α-keto acids with bromoacetylenes is catalyzed by hypervalent iodine(III) reagents when irradiation by sunlight at room temperature. The product ynones are generated in good yields. Experiments show that results obtained with blue light (λ=450-455 nm) are comparable to those obtained when using sunlight. Mechanistic studies demonstrate that the sunlight-driven decarboxylation undergoes a radical process.