A New Synthetic Approach to 4(1H)-Pyridone Derivatives. I. 1-Alkyl-3,5-diaryl-4(1H)-pyridones

Abdulla, Riaz F.; Emmick, Thomas L.; Taylor, H. M.

doi:10.1080/00397917708050752

Cited by 18 publications

(6 citation statements)

References 4 publications

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“…In the late 1970s, the exchange of amine moieties on enaminone structures was reported. 183 Later in the 1990s, similar exchanges between dialkylamine-derived enaminones and aromatic primary amines were discussed. 184,185 However, this exchangeable bond was not been implemented in polymers until 2014.…”

Section: Vinylogous Urethanes Ureas and Amidesmentioning

confidence: 99%

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

et al. 2021

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Vitrimers constitute a fascinating class of polymer materials which make the link between the historically opposed 3D networks (thermosets) and linear polymers (thermoplastics). Their chemical resistance, reshaping ability and unique rheological behavior upon heating make them promising for future applications in industry. However many vitrimers require the use of high catalyst loadings, which raises concerns for their durability, and limits their potential applications. To cope with this issue, internal catalysis and neighboring group participation (NGP) can be used to enhance the reshaping ability of such materials. A few studies report the effect of activating groups on the exchange reactions in vitrimers. Nevertheless, knowledge on this topic remains scarce, although research on vitrimers would greatly benefit from NGP already known in organic chemistry. The present perspective article presents the different types of exchangeable bonds implemented in vitrimers and discusses chemical groups known to have or potentially capable of an enhancing effect on exchange reactions. This analysis is underpinned by a thorough mechanistic discussion of the various exchangeable bonds presented.

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Section: Vinylogous Urethanes Ureas and Amidesmentioning

confidence: 99%

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

et al. 2021

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“…Moreover, insertion of a vinyl group into urethane moieties has drawn attention as a way of controlling timescales of polymer materials (Scheme 3d). This insertion of a vinyl group enables urethanes to undergo associative transamination reactions at elevated temperatures without added catalyst [83, 84] . The effect caused by this insertion can stabilize the vinylogous urethane linkages, thermodynamically creating an α,β‐unsaturated carbonyl moiety.…”

Section: Urethanes/ureamentioning

confidence: 99%

“…This insertion of a vinyl group enables urethanes to undergo associative transamination reactions at elevated temperatures without added catalyst. [83,84] The effect caused by this insertion can stabilize the vinylogous urethane linkages, thermodynamically creating an α,β-unsaturated carbonyl moiety. This moiety has high reactivity towards Michael-type reactions with excellent hydrolytic stability.…”

Section: Urethanes/ureamentioning

confidence: 99%

Dynamic Bonds: Adaptable Timescales for Responsive Materials

2022

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Dynamic bonds introduce unique properties such as self-healing, recyclability, shape memory, and malleability to polymers. Significant efforts have been made to synthesize a variety of dynamic linkers, creating a diverse library of materials. In addition to the development of new dynamic chemistries, fine-tuning of dynamic bonds has emerged as a technique to modulate dynamic properties. This Review highlights approaches for controlling the timescales of dynamic bonds in polymers. Particularly, eight dynamic bonds are considered, including urea/urethanes, boronic esters, Thiol-Michael exchange, Diels-Alder adducts, transesterification, imine bonds, coordination bonds, and hydrogen bonding. This Review emphasizes how structural modifications and external factors have been used as tools to tune the dynamic character of materials. Finally, this Review proposes strategies for tailoring the timescales of dynamic bonds in polymer materials through both kinetic effects and modulating bond thermodynamics.

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“…The latter undergo cyclization with the hydrochlorides of primary aliphatic amines, e.g., methylamine hydrochloride in boiling ethanol, to the pyridone carboxylic acid esters 199, which are hydrolyzed in the usual way to the corresponding carboxylic acids 200 (ABDULLA et al 1977a;Fig. The latter undergo cyclization with the hydrochlorides of primary aliphatic amines, e.g., methylamine hydrochloride in boiling ethanol, to the pyridone carboxylic acid esters 199, which are hydrolyzed in the usual way to the corresponding carboxylic acids 200 (ABDULLA et al 1977a;Fig.…”

Section: Synthesis Of 4-cinnolone-3-carboxylic Acidsmentioning

confidence: 99%

The Chemistry of the Quinolones: Methods of Synthesizing the Quinolone Ring System

Grohe¹

1998

Quinolone Antibacterials

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A New Synthetic Approach to 4(1H)-Pyridone Derivatives. I. 1-Alkyl-3,5-diaryl-4(1H)-pyridones

Cited by 18 publications

References 4 publications

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

Dynamic Bonds: Adaptable Timescales for Responsive Materials

The Chemistry of the Quinolones: Methods of Synthesizing the Quinolone Ring System

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