Benzoxazinone synthesis via Passerini–Smiles couplings

Benzoxazinones are easily prepared using Passerini–Smiles couplings of o-nitrophenol derivatives. Palladium-catalyzed flow-hydrogenation of adducts gives aniline derivatives that cyclize into benzoxazinones on treatment with trifluoroacetic acid.

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 37; pp. 5144 - 5146
Main Authors Martinand-Lurin, Elodie, El Kaïm, Laurent, Grimaud, Laurence
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.09.2014
Elsevier
Subjects
Benzoxazinone
Chemical Sciences
Chemistry
Chemistry, Organic
Hydrogenation
Isocyanide
Multicomponent reaction
Organic chemistry
Passerini–Smiles
Physical Sciences
Science & Technology
Passerini–Smiles
Benzoxazinone
Multicomponent reaction
Isocyanide
Hydrogenation
Passerini-Smiles
MULTICOMPONENT REACTIONS
DESIGN
BENZOXAZOLES
BENZIMIDAZOLES
DERIVATIVES
ACCESS
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Summary:Benzoxazinones are easily prepared using Passerini–Smiles couplings of o-nitrophenol derivatives. Palladium-catalyzed flow-hydrogenation of adducts gives aniline derivatives that cyclize into benzoxazinones on treatment with trifluoroacetic acid.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.07.088