Aliphatic Alcohol Hydroxyl‐Directed One‐Pot Stepwise Synthesis: A Concise Synthesis of 1H‐pyrrolo[3,4‐b]quinoline‐1,3(2H)‐diones

Huang, Shuntao; Yang, Qing; Wan, Juan; Wang, Z.; Zhou, Zhen; Li, Teng; Huang, Chao

doi:10.1002/adsc.202300453

Adv Synth Catal

2023

DOI: 10.1002/adsc.202300453

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Aliphatic Alcohol Hydroxyl‐Directed One‐Pot Stepwise Synthesis: A Concise Synthesis of 1H‐pyrrolo[3,4‐b]quinoline‐1,3(2H)‐diones

Shuntao Huang

Qing Yang

Juan Wan³

et al.

Abstract: A concise and flexible protocol to assemble structurally diverse 1H‐pyrrolo[3,4‐b]quinoline‐1,3(2H)‐diones (29 examples, 70–87% yields) has been developed via one‐pot stepwise synthesis. The potentially valuable quinine‐fused heterocycles were synthetized by utilizing aliphatic alcohol hydroxyl as directing group which promoted a sequential transformation to form functionalized aminomaleimides, and then underwent an I2‐oxidized tandem annulations. This route involved the formation of multiple new chemical bond… Show more

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Cited by 5 publications

References 30 publications

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Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Zhang,

Wan,

Yin

et al. 2024

Adv Synth Catal

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A substrate‐induced synthesis of coumarin‐fused quinolinones is achieved from 4‐(phenylamino)‐2H‐chromen‐2‐ones using N‐alkyl amines as the solvent and a carbon source under air conditions without any catalysts in one pot. This protocol highlights the special roles of 4‐(phenylamino)‐2H‐chromen‐2‐ones which were not only used as reactants but also as an internal oxidant selectively activated N‐α‐C(sp3)–H bond. This reaction features catalyst‐free, broad substrate scopes (N‐alkyl amines 27 examples and quinolinones 24 examples), operationally simple for the one‐step synthesis, and recovery and recycling of the solvent.

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Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Zhang,

Wan,

Yin

et al. 2024

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

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Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

Liu,

He,

et al. 2024

ChemistrySelect

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A concise and practicable route to the synthesis of multisubstituted 2‐pyridones via a four‐component one‐pot stepwise cyclization catalyzed by Cs2CO3 has been developed. During this stepwise transformation, two new C‐C bonds and two new C‐N bonds were generated through an intermolecular condensation/aza‐Michael reaction/intermolecular Michael addition/intramolecular cyclization sequence. The alternative protocol offers a complementary route to provide a series of structurally diverse polysubstituted 2‐pyridones (21 examples) in good to excellent yields (52–81%) from easily available raw materials arylamines, dialkyl acetylenedicarboxylate, 1,3‐dicarbonyl compounds, and trialkyl orthoformate under mild conditions. It might provide new opportunities for the discovery of 2‐pyridones‐containing drugs.

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Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp³)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine

Yin,

Zhang,

Huang

et al. 2024

J. Org. Chem.

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A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides and N-alkyl amines. The substrate and acidic additives were employed to cleave the C(sp 3 )−N bond as a onecarbon synthon for C−C and C−O coupling, thus facilitating the [n + 1] cascade cyclization reaction, which enabled the construction of seven-and eight-membered N,O-heterocycles at room temperature. The method exhibits abroad substrate scope and remarkable tolerance toward various functional groups (seven-membered 28 examples, eight-membered 8 examples, and activated Nalkyl amine 12 examples) and utilization of natural products (2 examples).

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Aliphatic Alcohol Hydroxyl‐Directed One‐Pot Stepwise Synthesis: A Concise Synthesis of 1H‐pyrrolo[3,4‐b]quinoline‐1,3(2H)‐diones

Cited by 5 publications

References 30 publications

Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp³)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine

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Aliphatic Alcohol Hydroxyl‐Directed One‐Pot Stepwise Synthesis: A Concise Synthesis of 1H‐pyrrolo[3,4‐b]quinoline‐1,3(2H)‐diones

Cited by 5 publications

References 30 publications

Substrate‐induced Selective α‐C(sp3)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Substrate‐induced Selective α‐C(sp3)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Cs2CO3‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp3)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine

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Product

Resources

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Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Substrate‐induced Selective α‐C(sp³)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air

Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp³)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine