A Mild and Efficient One-Pot Synthesis of 2-Aminated Benzoxazoles and Benzothiazoles

Previous syntheses of the biologically active 2-aminated benzoxazoles have relied on forcing thermal conditions to generate the products directly from the corresponding thiols. The resulting yields have ranged from moderate to poor. A mild and high-yielding alternative one-pot chlorination−amination...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-04, Vol.74 (8), p.3229-3231
Main Authors: Stewart, Gavin W, Baxter, Carl A, Cleator, Ed, Sheen, Faye J
Format: Article
Language:English
Subjects:
Amination
Benzothiazoles - chemical synthesis
Benzothiazoles - chemistry
Benzoxazoles - chemical synthesis
Benzoxazoles - chemistry
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Hydrocarbons, Halogenated - chemistry
Magnetic Resonance Spectroscopy - methods
Molecular Structure
Organic chemistry
Preparations and properties
Structure-Activity Relationship
Sulfhydryl Compounds - chemistry
Temperature
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Summary:Previous syntheses of the biologically active 2-aminated benzoxazoles have relied on forcing thermal conditions to generate the products directly from the corresponding thiols. The resulting yields have ranged from moderate to poor. A mild and high-yielding alternative one-pot chlorination−amination procedure is described. Compounds with a variety of substitution patterns are reported and the methodology has been successfully extended to benzothiazoles. Palladium catalysis on suitably activated examples has been employed to generate the desired compounds of interest.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900308t