Synthesis of γ‐ and β‐Carbolines via Diphenyl Phosphate‐Mediated Condensation of 3/2‐Carbonyl‐2/3‐Vinylindoles with Phenyl Hydrazine Followed by Electrocyclization DOI
Rudrasenan Agneswaran, Arasambattu K. Mohanakrishnan

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(46)

Published: Dec. 1, 2024

Abstract A facile synthesis of 3‐alkyl‐2‐aryl substituted γ‐carboline derivatives is reported involving diphenyl phosphate catalyzed condensation 3‐(acetyl/propionyl)‐2‐(nitroaryl)vinyl‐1‐phenylsulfonylindoles with phenyl hydrazine followed by concurrent electrocyclization and aromatization through elimination aniline. This strategy could be successfully explored 1‐phenylsulfonylindole‐3/2‐carboxaldehydes containing vinyl unit at 2/3‐position to afford the respective γ‐and β‐carboline derivatives. The domino reaction easily accessible 2/3‐carbonyl indoles a adjacent positions as an amine source afforded wide variety carboline in good acceptable yields. synthetic utility representative demonstrated via transformation into corresponding indolo[a]carboline framework.

Language: Английский

One-Step Synthesis of Indoloquinoline Alkaloids via the Pd-Catalyzed Larock/Ligand-Accelerated C–H Activation Cascade Reaction DOI
Chien‐Huang Wu, Jinjian Li,

Hongyu Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 16, 2025

Pd-catalyzed cascade annulation of 2-iodoanilines with N,3-diphenylpropiolamides was achieved, which afforded a series indolo[2,3-c]quinolinones good yields and functional group compatibility. Previously, the retro-synthetic routine for indolo[2,3-c]quinolinone skeleton has often involved intramolecular disconnection C(sp2)-C(sp2) bond at variable positions, necessitates construction an indole or quinoline reactant multiple pre-set functionalities. Meanwhile, using C-H activation strategy to construct indoloquinoline is limited cases in must be bearing nonremovable directing group. Therefore, circumvent these limitations, we herein report Larock/ligand-accelerated one-pot fashion. This transformation 2-amidoindole relies on Larock reaction, then forms C-N afford via ligand-enabled activation.

Language: Английский

Citations

0
Synthesis of γ‐ and β‐Carbolines via Diphenyl Phosphate‐Mediated Condensation of 3/2‐Carbonyl‐2/3‐Vinylindoles with Phenyl Hydrazine Followed by Electrocyclization DOI
Rudrasenan Agneswaran, Arasambattu K. Mohanakrishnan

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(46)

Published: Dec. 1, 2024

Abstract A facile synthesis of 3‐alkyl‐2‐aryl substituted γ‐carboline derivatives is reported involving diphenyl phosphate catalyzed condensation 3‐(acetyl/propionyl)‐2‐(nitroaryl)vinyl‐1‐phenylsulfonylindoles with phenyl hydrazine followed by concurrent electrocyclization and aromatization through elimination aniline. This strategy could be successfully explored 1‐phenylsulfonylindole‐3/2‐carboxaldehydes containing vinyl unit at 2/3‐position to afford the respective γ‐and β‐carboline derivatives. The domino reaction easily accessible 2/3‐carbonyl indoles a adjacent positions as an amine source afforded wide variety carboline in good acceptable yields. synthetic utility representative demonstrated via transformation into corresponding indolo[a]carboline framework.

Language: Английский

Citations

0