Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides DOI
Feng Li, Qing Yang,

He Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11567 - 11575

Published: Aug. 1, 2024

An effective and straightforward Ag(I)-mediated annulation of 2-(2-enynyl)quinolines N'-(2-alkynylbenzylidene)hydrazides was developed, forging various synthetically challenging 17bH-isoquinolino[2'',1'':1′,6']pyridazino[4′,5′:3,4]pyrrolo[1,2-a]quinolines, including different nitrogen-containing fused rings, in moderate to excellent yields. This one-pot cycloaddition strategy features exclusive regioselectivity, high atom economy, broad substrate scope under mild conditions. The practicality reliability this reaction demonstrated by a successful scale-up synthesis.

Language: Английский

Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements DOI
P. Devi, Mohan Neetha, Gopinathan Anilkumar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(21), P. 4332 - 4357

Published: Jan. 1, 2023

Silver catalysis offers environmentally friendly and simple protocols to construct N-heterocycles. Inspired by its appeal, herein we have summarized developments in the silver-catalyzed synthesis of N-heterocycles since 2019.

Language: Английский

Citations

12
Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts DOI
Farhad Golmohammadi, Chiman Osmani,

Frank Röminger

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 19, 2025

A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- oxidant-free [3 + 2] cycloaddition reaction zwitterionic ketenimines pyridinium salts. This versatile method proceeds under mild conditions, affording in moderate to good yields. approach involves an intermolecular cycloaddition, followed by enamine/imine tautomerization aromatization. Notably, this demonstrates broad functional group compatibility allows facile scalability, making it valuable tool indolizine-based frameworks organic medicinal chemistry.

Language: Английский

Citations

0
Ag(I)-Mediated Annulation of 2-(2-Enynyl)pyridines and Propargyl Amines to Access 1-(2H-Pyrrol-3-yl)indolizines DOI
Feng Li, Qing Yang, Mingyue Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 304 - 312

Published: Dec. 21, 2023

An effective Ag(I)-mediated annulation of 2-(2-enynyl)pyridines and propargyl amines was developed, unexpectedly affording a broad range functionalized 1-(2H-pyrrol-3-yl)indolizines in moderate to excellent yields. The developed method is characterized by operational simplicity, ready availability starting materials, high regioselectivity, substrate scope under mild reaction conditions. Ag(I)-promoted cyclization possibly results the formation spiroindolizine, ring-opening rearrangement which may give 1-(2H-pyrrol-3-yl)indolizine. Furthermore, gram-scale synthetic transformations are also studied.

Language: Английский

Citations

4
Metal/catalyst/alkyne/alkene‐free one‐pot synthesis of indolizines from 2‐(pyridin‐2‐yl)acetate, DMF‐DMA and α‐halomethylenes DOI
Hitesh B. Jalani,

Doha Lee,

Ju‐Young Lee

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2023, Volume and Issue: 60(5), P. 825 - 833

Published: Feb. 9, 2023

Abstract We have described a simple and robust one‐pot synthesis of 1,3‐disubstitued‐indolizines from 2‐(pyridin‐2‐yl)acetate, DMF‐DMA α‐halomethylenes without using metal/catalyst/alkyne/alkene. This protocol provides variety indolizine analogs via in‐situ formed 3‐(dimethylamino)‐2‐(pyridin‐2‐yl)acrylate intermediate, undergoes N‐alkylation followed by Michael addition/cyclization. The gram scale developed this does not require chromatographic purification. post application alkyne bearing provided triazole beta‐ketoester containing indolizine‐tethered pyrimidine heterocyclic system.

Language: Английский

Citations

2
Organocatalyzed Double C(sp3)−H Alkylation of Cyclic N‐Sulfonyl Ketimines with 3‐Chloropropiophenones: Selective Access to 2,3,6‐Trisubstituted Pyridines DOI
Ashvani K. Patel, Sampak Samanta

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(33)

Published: July 11, 2023

Abstract An efficient sequential one‐pot, two‐step pseudo‐four‐component reaction between 3/4‐methyl N ‐sulfonyl ketimines with 3‐chloropropiophenones triggered by DIPEA/NaHCO 3 as a cooperative base and subsequent aza‐cyclization using NH 4 OAc is reported. This transition‐metal‐oxidant‐free technique concocts new C−C/C=C/C=N−C bonds selectively, guaranteeing acceptable yields of 2,3,6‐trisubstituted pyridines possessing ortho ‐hydroxyaryl/benzenesulfonamide propiophenone moieties at C2 C3 positions, respectively. Interestingly, while replacing methyl‐substituents straight alkyl chains ketimines, only monoalkylation happened in situ‐generated vinyl ketones to deliver promising 3‐picoline derivatives. Moreover, the synthetic transmutation prepared pyridine derivative led several important classes pyridocoumarin, 5 H ‐chromenopyridine, di(pyridin‐3‐yl) methane

Language: Английский

Citations

1
Gold-catalyzed intermolecular tandem cyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines DOI

Fucai Rao,

Meng Cheng,

Zhiwei Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3685 - 3691

Published: Jan. 1, 2024

A new method for the synthesis of seven-membered heterocycle-fused indolizine scaffolds from 2-(1-alkynyl-cyclopropyl)pyridines and nitrones under catalysis PPh 3 AuNTf 2 .

Language: Английский

Citations

0
Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides DOI
Feng Li, Qing Yang,

He Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11567 - 11575

Published: Aug. 1, 2024

An effective and straightforward Ag(I)-mediated annulation of 2-(2-enynyl)quinolines N'-(2-alkynylbenzylidene)hydrazides was developed, forging various synthetically challenging 17bH-isoquinolino[2'',1'':1′,6']pyridazino[4′,5′:3,4]pyrrolo[1,2-a]quinolines, including different nitrogen-containing fused rings, in moderate to excellent yields. This one-pot cycloaddition strategy features exclusive regioselectivity, high atom economy, broad substrate scope under mild conditions. The practicality reliability this reaction demonstrated by a successful scale-up synthesis.

Language: Английский

Citations

0