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Synfacts 2011(2): 0139-0139  
DOI: 10.1055/s-0030-1259384
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-Aminobenzoxazoles from 2-Aminophenols

Contributor(s): Victor Snieckus, Matthew O. Kitching
C. L. Cioffi*, J. J. Lansing, H. Yüksel
AMRI, Albany, USA
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

Reported is the synthesis of 2-aminobenzoxazoles from the corresponding 2-aminophenols using orthocarbonate lynchpin reagents. Broad scope for the reaction was established, with cyclic secondary amines giving the highest yields, while volatile or hindered amines performed poorly. Substitution of the amino­phenol component is well tolerated. The use of 1,1-dichlorodiphenoxymethane in place of the ­orthocarbonate proved efficacious when side reactions such as amide formation were observed.