A new synthesis of highly functionalized oxazoles

Functionalized oxazoles and bis-oxazoles are obtained by side-chain oxidation of beta-hydroxy amides with the Dess-Martin periodinane, followed by cyclodehydration with triphenylphosphine/iodine in the presence of triethylamine.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 58; no. 14; pp. 3604 - 3606
Main Authors Wipf, Peter, Miller, Chris P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.1993
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
OXIDATION
MARINE METABOLITES
ALPHA-AMINO
NUDIBRANCH EGGMASSES
ALDEHYDES
DERIVATIVES
MACROLIDES
Cyclodehydration
α-Aminoacid
Five membered ring
Base catalysis
Hydroxyamide
Oxidation
Oxygen nitrogen heterocycle
Iodine
Online AccessGet full text
ISSN0022-3263
1520-6904
DOI10.1021/jo00066a004

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Summary:Functionalized oxazoles and bis-oxazoles are obtained by side-chain oxidation of beta-hydroxy amides with the Dess-Martin periodinane, followed by cyclodehydration with triphenylphosphine/iodine in the presence of triethylamine.
Bibliography:ark:/67375/TPS-R5T8LX5Q-2
istex:2CA1461ECD79EA1A0ABF9CB911A459C2F12B621C
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00066a004