A modified Pudovik reaction, self-catalysis synthesis of 3-phosphinoylindoles

Li, Guofeng; Gao, Jigang; Zhang, Heng; Qin, Xiangshuo; Guan, Xiangjiu; Jiang, Guofeng; Zhang, Guangliang; Zhang, Suoqin

doi:10.1016/j.tetlet.2019.06.043

Cited by 11 publications

(4 citation statements)

References 60 publications

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“…3-Hydroxy-3-indolyloxindoles 473 act as excellent electrophiles in a self-catalyzed reaction reported by Zhang’s research group (Scheme ). These compounds react with nucleophiles like diethyl phosphite ( 417 ) to afford the corresponding 3-phosphinoylindoles 474 in excellent yields via a Pudovik reaction mechanism where the imides are replaced by 3-hydroxy-3-indolyloxindoles 473 …”

Section: Five-membered Rings: Nonaromatic Aromatic and Benzo-fused He...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search in the development of synthetic routes for obtaining novel members of this family of compounds. This updated review covers methodologies established since 2004, focusing on the synthesis of azaheterocyclic phosphonates, of which the phosphonate moiety is directly substituted onto to the azaheterocyclic structure. Emphasizing recent advances, this review classifies newly developed synthetic approaches according to the ring size and providing information on biological activities whenever available. Furthermore, this review summarizes information on various methods for the formation of C–P bonds, examining sustainable approaches such as the Michaelis–Arbuzov reaction, the Michaelis–Becker reaction, the Pudovik reaction, the Hirao coupling, and the Kabachnik–Fields reaction. After analyzing the biological activities and applications of azaheterocyclic phosphonates investigated in recent years, a predominant focus on the evaluation of these compounds as anticancer agents is evident. Furthermore, emerging applications underline the versatility and potential of these compounds, highlighting the need for continued research on synthetic methods to expand this interesting family.

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Section: Five-membered Rings: Nonaromatic Aromatic and Benzo-fused He...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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“…Recently, Zhang and co‐workers studied the reaction of isatin‐derived 3‐indolylmethanols 64 and diethyl phosphonate 37a under catalyst‐free conditions at room temperture . They proposed that a possible modified Pudovik reaction pathway with a self‐catalysis system diversely delivered C‐3 phosphonated oxindoles 65 in high yields (Scheme ).…”

Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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“…The synthetic potential of autocatalysis has been exemplified in organometallic reactions ( Semenov et al., 2018 ; Flegeau et al., 2011 ). However, compared to the auto-catalysis, the organometallic reactions involving a self-catalytic cycle are rare ( Li et al., 2018 ; Wang et al., 2019 ; Bachmann et al., 2008 ; MacLeod et al., 2010 ; Liu et al., 2019 ; Rodrigues et al., 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Unlocking a self-catalytic cycle in a copper-catalyzed aerobic oxidative coupling/cyclization reaction

Liu

Wang

et al. 2022

iScience

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A modified Pudovik reaction, self-catalysis synthesis of 3-phosphinoylindoles

Cited by 11 publications

References 60 publications

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

Unlocking a self-catalytic cycle in a copper-catalyzed aerobic oxidative coupling/cyclization reaction

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