Palladium‐Catalyzed Propargylic [n+2] Cycloaddition: An Efficient Strategy for Construction of Benzo‐Fused Medium‐Sized Heterocycles

Liu, Zhen‐Ting; Hu, Xiang‐Ping

doi:10.1002/adsc.201801359

Cited by 4 publications

(1 citation statement)

References 80 publications

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“…The reaction shows a broad substrate scope (particularly in 9-membered ring series), excellent regio-and Z/E-selectivities (>95/5), and high yields. Another strategy that was recently published by Liu and Hu consisted of a Pd-catalyzed [n + 2] formal cycloaddition enabling access to medium-sized heterocycles from eight to eleven-membered rings [59]. Various linker-tethered-bisphenols 58 were used as n-atom (n = 6 to 9) bis-nucleophile partners in reaction with propargylic esters 59 as C2 synthons.…”

Section: Formal Cycloadditionmentioning

confidence: 99%

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

et al. 2020

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Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom.

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Section: Formal Cycloadditionmentioning

confidence: 99%

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

et al. 2020

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Copper‐Catalyzed One‐Pot Cascade Cyclization for the Synthesis of Isoindolo[2,1‐a]quinoxalines

Liu

2021

Adv Synth Catal

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A copper-catalyzed one-pot cascade cyclization of 2-(1-(acetyloxy)propargyl)benzaldehydes with o-phenylenediamines for an access to substituted isoindolo[2,1-a]quinoxalines has been developed. The reaction features readily available starting materials, simple operational procedure, and broad substrate scopes. Under optimal conditions, various isoindolo[2,1-a]quinoxalines were afforded in 41-88% yields.

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Investigation of the palladium-catalysed cyclisation of α-amido malonates with propargylic compounds

Barlow

Franckevičius

2021

Tetrahedron

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Palladium‐Catalyzed Propargylic [n+2] Cycloaddition: An Efficient Strategy for Construction of Benzo‐Fused Medium‐Sized Heterocycles

Abstract: No Abstract

Cited by 4 publications

References 80 publications

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Copper‐Catalyzed One‐Pot Cascade Cyclization for the Synthesis of Isoindolo[2,1‐a]quinoxalines

Investigation of the palladium-catalysed cyclisation of α-amido malonates with propargylic compounds

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