Oxazoles Are Masked Carboxyls That Activate Ortho-Leaving Groups in Nucleophilic Aromatic Substitution

doi:10.1246/CL.1987.19

Paper

Oxazoles Are Masked Carboxyls That Activate Ortho-Leaving Groups in Nucleophilic Aromatic Substitution

Published Jan 5, 1987 · D. Cram, J. Bryant, K. Doxsee

Chemistry Letters

Q2 SJR score

12

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0

Influential Citations

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Abstract

Oxazoles substituted in their 2-positions with 2-methoxy-, 2-fluoro-, or 2,6-difluorophenyl groups, and in their 4,5-positions with methyls or phenyls, were treated with ArMgBr or ArLi to give substituted biphenyl or terphenyl products. The oxazole groups were subsequently converted to esters, acids, or amides. These reactions provide a new unsymmetrical aryl-aryl coupling synthon.

Study Snapshot

Oxazoles with substituted groups can activate ortho- leaving groups in nucleophilic aromatic substitution, providing a new unsymmetrical aryl-aryl coupling synthon.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Oxazoles Are Masked Carboxyls That Activate Ortho-Leaving Groups in Nucleophilic Aromatic Substitution

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References

Activated carboxylates from the photooxygenation of oxazoles : Application to the synthesis of recifeiolide, curvularin and other macrolides

Photooxygenation of oxazoles can produce activated carboxylates, which can be used for the synthesis of macrolides like recifeiolide and curvularin.

Citations

Synthesis of 2,4,5-Trisubstituted Oxazoles from Copper-Mediated Benzylic sp3 C-H Aerobic Oxidative Annulation of Ketones and Amines via a Cascade Reaction.

Copper-catalyzed oxidative annulation of ketones and amines effectively synthesizes 2,4,5-trisubstituted oxazoles, offering potential for potent organic compounds.

Mild base-promoted benzannulation for the construction of polyfunctionalized m-terphenyl derivatives and their application as potent UV-filters

This study developed a simple, transition-metal-free benzannulation method for constructing polyfunctionalized m-terphenyl derivatives, which can be used as potent UV-filters.

Indium-Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2-Methyl-3-(thien-2-yl)-1H-indole

Indium-catalyzed SNAr reaction allows for the synthesis of 2-methyl-3-(thien-2-yl)-1H-indole on a large-scale, with 2-methoxythiophene being used as a molar excess for purification.

2‐(o‐Methoxyphenyl)‐4,4‐dimethyl‐2‐oxazoline

2-(o-Methoxyphenyl)-4,4-dimethyl-2-oxazoline is a compound used in the electrophilic arylation of Grignard reagents, lithium reagents, and lithium amides for synthesizing various organic compounds.

Some Synthetic Uses of Halides

Halides can be used for carbon-carbon bond formation, amine formation, alcohol and thiol formations, ether and sulfide formations, and rearrangement of halides.

The chemistry of 2-oxazolines (1985–present)

2-Oxazolines have revolutionized synthetic organic chemistry by serving as versatile protecting groups, coordinating ligands, and activating moities, with applications in polymer production, analytical processes, and medicinal chemistry.