Microwave Assisted Synthesis of Five Membered Azaheterocyclic Systems

A sequential one‐pot method for the synthesis of 4‐(hydroxymethyl)oxazoles from readily available benzamides has been developed. Various substituted benzamides well‐tolerated and furnished 4‐(hydroxymethyl)oxazoles in moderate to good yields under the present reaction conditions. In order to demonstrate the usefulness of the present methodology, the resulting 4‐(hydroxymethyl)oxazoles were successfully transformed into its corresponding phosphonates under Michaelis‐Arbuzov reaction conditions. This methodology features a broad substrate scope, step economy, ease of execution, and scalability.

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Sequential One‐pot Method for the Synthesis of 4‐(Hydroxymethyl)oxazoles and their Application in Phosphonates Synthesis

Kajol

Ramesh

2021

Asian J Org Chem

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Synthesis of Substituted Oxazoles from N‐Benzyl Propargyl Amines and Acid Chlorides

Wachenfeldt¹,

Paulsen²,

Sundin³

et al. 2013

Eur J Org Chem

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The reaction between N‐benzylpropargylamines and acid chlorides at elevated temperatures provides efficient, direct access to a variety of di‐ and tri‐substituted oxazoles. The versatility of this reaction is explored and 21 examples are demonstrated. The usefulness of the methodology is showcased through the short and efficient formal syntheses of medicinally relevant drugs aleglitazar and romazarit.

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5‐Alkoxyoxazole – A Versatile Building Block in (Bio)organic Synthesis

et al. 2016

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The 5‐alkoxyoxazole ring system has proved to be a useful and versatile building block that is involved in a variety of chemical transformations (e.g., hetero‐Diels–Alder reactions, formal 1,3‐dipolar cycloadditions, photochemical [2+2] cycloadditions, Claisen rearrangements, and ring‐opening processes). 5‐Alkoxyoxazoles have provided synthetic access to heteroaromatic scaffolds such as pyridines, furans, oxadiazolines, pyrrolidines, and significant linear chemical patterns, including amino acid derivatives. This review focuses on the broad range of reactivity of 5‐alkoxyoxazoles and their subsequent applications to the syntheses of naturally occurring compounds and biologically active molecules.

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Microwave Assisted Synthesis of Five Membered Azaheterocyclic Systems

Cited by 26 publications

References 186 publications

Sequential One‐pot Method for the Synthesis of 4‐(Hydroxymethyl)oxazoles and their Application in Phosphonates Synthesis

Sequential One‐pot Method for the Synthesis of 4‐(Hydroxymethyl)oxazoles and their Application in Phosphonates Synthesis

Synthesis of Substituted Oxazoles from N‐Benzyl Propargyl Amines and Acid Chlorides

5‐Alkoxyoxazole – A Versatile Building Block in (Bio)organic Synthesis

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