Tetrahedron

An efficient synthesis of 7-hydroxy-2, 6-dimethylchromeno [3, 4-d] oxazol-4-one—a protected fragment of novenamine

DW Gammon, R Hunter, SA Wilson

Index: Gammon, David W.; Hunter, Roger; Wilson, Seanette A. Tetrahedron, 2005 , vol. 61, # 45 p. 10683 - 10688

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Citation Number: 18

Abstract

The high-yielding six-step synthesis of 7-hydroxy-2, 6-dimethylchromeno [3, 4-d] oxazol-4- one from commercially available 2, 4-dihydroxy-3-methylacetophenone is described. Coumarin constitutes a useful synthon for coumarin antibiotic synthesis. A new methodology for oxazole formation applicable to 3-aminocoumarins has been developed, and a mechanistic rationalization is proposed.