3274-61-1Relevant academic research and scientific papers
Visible Light-Induced, Metal-Free Denitrative [3+2] Cycloaddition for Trisubstituted Pyrrole Synthesis
Karki, Bhupal S.,Devi, Lalita,Pokhriyal, Ayushi,Kant, Ruchir,Rastogi, Namrata
, p. 4793 - 4797 (2019)
A metal-free, regioselective synthesis of trisubstituted pyrroles has been developed through a formal [3+2] cycloaddition reaction between 2H-azirines and nitroalkenes under visible light/photoredox-catalyzed conditions. The reaction proceeds through 2H-a
Photoredox-Enabled Chromium-Catalyzed Alkene Diacylations
Liu, Jing,Lu, Liang-Qiu,Luo, Yixin,Zhao, Wei,Sun, Peng-Chao,Jin, Weiwei,Qi, Xiaotian,Cheng, Ying,Xiao, Wen-Jing
, p. 1879 - 1885 (2022/02/07)
Transition-metal-catalyzed cross-coupling reactions are a powerful tool to construct carbon-carbon bonds in modern synthetic chemistry. Chromium catalysis is much less developed compared with the widely used palladium and nickel catalysis. Herein, we repo
Regioselective competitive synthesis of 3,5-bis(het) aryl pyrrole-2-carboxylates/carbonitriles vs. β-enaminones from β-thioxoketones
Sharath Kumar, Kothanahally S.,Ananda, Hanumappa,Rangappa, Shobith,Raghavan, Sathees C.,Rangappa, Kanchugarakoppal S.
supporting information, (2021/09/28)
An easily adaptable protocol for the synthesis of 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles and the related 2,3,5-tri(het)aryl-pyrroles with complementary regioselectivity from the corresponding 1,3-bis(het)aryl-1,3-monothio diketones or β-enaminone precursors has been reported. Initially, regioselective base catalyzed condensation of glycine ethyl/methyl esters or aminoacetonitrile with 1,3-bis(het)aryl-1,3-monothio diketones give β-enaminones, which then in-situ undergoes cyclization to form 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles. The synthesis of 2,3,5 tri substituted pyrroles with full control over 3rd & 5th position on pyrrole ring is the noteworthy feature of this protocol. Although the product yields are moderate to good, the method offers a facile regioselective entry to 2,3,5 trisubstituted pyrroles without the aid of transition metal.
One-Pot Synthesis of N-H-Free Pyrroles from Aldehydes and Alkynes
Chen, Lai,Huo, Jing-Qian,Kou, Song,Mao, Jianyou,Si, He-Long,Xu, Xin-Yu,Zhang, Jin-Lin
supporting information, p. 4348 - 4352 (2021/06/27)
The first base-mediated intermolecular cyclization of arylaldehydes and terminal arylacetylenes for the synthesis of a wide range of pyrroles in a single step has been described. The developed methodology used commercially available starting materials and
Synthesis of 2,2,5-Trisubstituted 2 H-Pyrroles and 2,3,5-Trisubstituted 1 H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation
Yamaguchi, Miyuki,Fujiwara, Sakiko,Manabe, Kei
, p. 6972 - 6977 (2019/09/03)
Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-arylated 2,3,5-triaryl-1H-pyrroles were prepared. The obtained 2,2,5-triaryl-2H-pyrroles could be further transformed into 2,2,5,5-tetraarylpyrrolidines.
One-pot synthesis of 2,3,5-substituted 1H-pyrroles via the reaction of terminal acetylenes with nitriles and EtAlCl2 catalyzed by Сp2TiCl2
Khafizova, Leila O.,Shaibakova, Mariya G.,Rikhter, Nikita A.,Tyumkina, Tatyana V.,Dzhemilev, Usein M.
, p. 906 - 911 (2019/01/11)
A new one pot method for the synthesis of 2,3,5-substituted 1H-pyrroles in moderate to good yields (58–77%) based on multicomponent reaction of terminal acetylenes with nitriles and EtAlCl2 in the presence of Сp2TiCl2 cata
General Transition Metal-Free Synthesis of NH-Pyrroles from Secondary Alcohols and 2-Aminoalcohols
Krasniqi, Besir,Geerts, Kayle,Dehaen, Wim
, p. 5027 - 5034 (2019/05/10)
A novel, transition metal-free and one-pot methodology to synthesize various substituted NH-pyrroles from readily available building blocks such as secondary alcohols and 2-aminoalcohols is described. The process is based on the venerable Oppenauer-Woodward oxidation, which uses benzophenone as an inexpensive reagent to achieve oxidation of secondary alcohols under mild condition to ketones, further in situ condensation with aminoalcohol, and oxidative cyclization to the target pyrrole ring. The reaction occurs under basic conditions, and features a broad substrate scope combined with very good tolerance for sensitive functional groups. This method can be used to synthesize various substituted pyrroles useful as a starting material for broad applications.
Iron-Catalyzed Radical Cycloaddition of 2H-Azirines and Enamides for the Synthesis of Pyrroles
Zhao, Mi-Na,Ren, Zhi-Hui,Yang, De-Suo,Guan, Zheng-Hui
, p. 1287 - 1290 (2018/03/09)
A novel and efficient Fe-catalyzed radical cycloaddition of 2H-azirines and enamides for the synthesis of substituted pyrroles has been developed. The radical cycloaddition reaction proceeded through a conceptually new Fe(II)-catalyzed homolytic cleavage of C-N bond of 2H-azirines sequential radical cyclization with enamides. The reaction used readily available starting materials, tolerated various functional groups, and afforded valuable triaryl-substituted pyrroles in good to high yields under mild reaction conditions.
4-pyrroline-2-ketone derivative and preparation method thereof
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Paragraph 0040-0042, (2018/12/13)
The invention belongs to the technical field of medicine and particularly relates to a 4-pyrroline-2-ketone derivative and a preparation method thereof. The method comprises the following reaction step that a pyrrole compound as shown in the formula (1) reacts in the presence of a solvent, alkali and oxygen, and thus the 4-pyrroline-2-ketone derivative as shown in the formula (2) is obtained. Theraw materials used in the preparation method are easy to obtain, the reaction conditions are mild, the product yield is high, the substrate application range is wide, the reaction specificity is high,post-treatment is easy and environmentally friendly, and thus the synthesis method of the 4-pyrroline-2-one derivative is novel and efficient. The formula (1) and the formula (2) are shown in the description.
Base-Promoted Oxidative Dearomatization of Pyrroles to 4-Pyrrolin-2-ones
Huang, Huabin,Hu, Bing,Lai, Yuanfa,Zou, Zhongai,Lin, Huixia,Xiao, Yujuan,You, Qihua,Shen, Jinhai
supporting information, p. 3906 - 3910 (2018/09/21)
A base-promoted oxidative dearomatization of substituted pyrroles for the synthesis of 3,3-disubstituted 4-pyrrolin-2-ones under mild reaction conditions is described. A cascade aerobic oxidation/semipinacol rearrangement reaction was involved, and the desired products bearing a quaternary carbon center were efficiently prepared using molecular oxygen (O2) as an ideal oxidant. (Figure presented.).
