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Synlett 2017; 28(05): 521-541
DOI: 10.1055/s-0036-1588671
DOI: 10.1055/s-0036-1588671
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A Decade Update on Benzoxazoles, a Privileged Scaffold in Synthetic Organic Chemistry
Further Information
Publication History
Received: 27 September 2016
Accepted after revision: 15 November 2016
Publication Date:
10 January 2017 (online)
Abstract
In 2014, more than 80% of the marketed drugs in the US contained heterocyclic compounds, which play a major role in the drug-discovery process, as one of the primary components. Benzoxazole, consisting of an oxazole ring fused with a benzene ring, has shown profound impact in drug discovery research owing to its important bioactivity. This moiety has also shown important properties in material science. The synthesis of this privileged scaffold from readily available chemicals remains a primary focus for the synthetic chemistry community. In this review, efforts have been made to focus on the latest information available on the different synthetic strategies such as solution phase, multicomponent, green and solid phase chemistry and applications of different benzoxazole derivatives. Furthermore, the updated synthetic information incorporated in this review article will help to improve future synthesis of this scaffold.
1 Introduction
2 Solution-Phase Synthetic Approach to Substituted Benzoxazoles
2.1 Condensation of o-Aminophenol with Carboxylic Acids
2.2 Condensation of o-Aminophenol with Aldehydes
2.3 Condensation of o-Aminophenol with Orthoesters, ortho-Haloamides, or 1,1-Dihaloalkenes
2.4 Synthesis of Benzoxazoles from Schiff Bases
2.5 Miscellaneous
3 Multicomponent Synthetic Approach to Substituted Benzoxazoles
4 Solid-Phase Synthetic Approach to Substituted Benzoxazoles
5 Green Synthetic Approach to Substituted Benzoxazoles
5.1 Condensation of o-Aminophenol with Aldehydes
5.2 Condensation of o-Aminophenol with ortho-Substituted Benzamides
5.3 Condensation of o-Aminophenol with Carboxylic Acid and its Derivatives
5.4 Condensation of o-Aminophenol with Alcohols or Amines
5.5 Miscellaneous
6 Bioactive Derivatives of Benzoxazoles
7 Conclusion and Outlook
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