C–C Bond Cleavage Mediated Reaction for Constructing 3-Carbonyl Imidazo[1,5-<i>a</i>] Pyridines from 1,3-Dicarbonyl Compounds and Pyridin-2-ylmethanamines

Wang, Qiang; Yao, Xia; Zhao, Peilan; Liu, Wanxiang; Zhao, Wangyan; Fang, Xin; Zhu, Yun; Dai, Gangqiang

doi:10.1021/acs.joc.3c01425

Cited by 2 publications

(1 citation statement)

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“…(Scheme b) Subsequently, Wang’s group utilized successfully an ammonium iodide-mediated sp 3 (C–H) double amination of acetophenones with 2-pyridinemethanamines to afford the desired products in one-step way by an electrochemical tandem process . (Scheme c) In 2023, Wang’s group reported a I 2 -mediated [4 + 1] cyclization reaction for constructing 3-acyl imidazo[1,5- a ]pyridines from 1,3-dicarbonyl compounds and pyridin-2-ylmethanamines . (Scheme d) In these abovementioned reports, we clearly found that all routes for the synthesis of 3-acyl imidazo[1,5- a ]pyridines employed pyridin-2-ylmethanamines as the substrates.…”

Section: Introductionmentioning

confidence: 99%

Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN₃ Using O₂ as the Oxygen Source

Chen,

Zhang,

Wang

et al. 2024

J. Org. Chem.

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Currently, most conventional methods to achieve imidazo [1,5-a]pyridines have limitations for the synthesis of 3-acyl imidazo[1,5-a]pyridines. Herein, a novel and efficient Cu(I)-catalyzed three-component annulation method for the synthesis of valuable 3-acyl imidazo[1,5-a]pyridines by the reaction of 2-pyridinyl-substituted p-QMs, terminal alkynes, and TsN 3 in the presence of O 2 under mild conditions have successfully been developed. The investigation indicated that molecular oxygen (O 2 ) and TsN 3 , respectively, serving as oxygen and nitrogen sources, were essential for the successful completion of the reaction system.

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Section: Introductionmentioning

confidence: 99%

Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN₃ Using O₂ as the Oxygen Source

Chen,

Zhang,

Wang

et al. 2024

J. Org. Chem.

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Reconstructive Synthesis of Fluorinated Dihydropyrido[1,2‐a] indolones by a Cyclohexadione Cut‐to‐Fuse Strategy

China,

Yoto,

Sasa

et al. 2024

Adv Synth Catal

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We describe a fluorinative ring‐cleavage reaction that breaks C–C bonds in cyclic β‐diketones bearing aryl moiety using N‐fluorobenzenesulfonimide (NFSI) in the presence of inorganic carbonates (Cs2CO3 or K2CO3) in methanol at room temperature within one hour. Generated fluorinated keto acid esters bearing ortho‐nitro aryl groups were transformed into fluorinated dihydropyrido[1,2‐a]indolones (DHPIs) via reductive cyclization using B2(OH)4 followed by amidation in the presence of K2CO3. This "cut‐to‐fuse" strategy enables the reconstructive synthesis of valuable fused heterocycles from relatively simple cyclohexadione.

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C–C Bond Cleavage Mediated Reaction for Constructing 3-Carbonyl Imidazo[1,5-a] Pyridines from 1,3-Dicarbonyl Compounds and Pyridin-2-ylmethanamines

Cited by 2 publications

References 19 publications

Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN₃ Using O₂ as the Oxygen Source

Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN₃ Using O₂ as the Oxygen Source

Reconstructive Synthesis of Fluorinated Dihydropyrido[1,2‐a] indolones by a Cyclohexadione Cut‐to‐Fuse Strategy

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C–C Bond Cleavage Mediated Reaction for Constructing 3-Carbonyl Imidazo[1,5-a] Pyridines from 1,3-Dicarbonyl Compounds and Pyridin-2-ylmethanamines

Cited by 2 publications

References 19 publications

Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN3 Using O2 as the Oxygen Source

Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN3 Using O2 as the Oxygen Source

Reconstructive Synthesis of Fluorinated Dihydropyrido[1,2‐a] indolones by a Cyclohexadione Cut‐to‐Fuse Strategy

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Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN₃ Using O₂ as the Oxygen Source

Cu(I)-Catalyzed Three-Component Annulation for the Synthesis of 3-Acyl Imidazo[1, 5-a]Pyridines from 2-Pyridinyl-Substituted p-Quinone Methides, Terminal Alkynes, and TsN₃ Using O₂ as the Oxygen Source