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Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement.

ABSTRACT: N-Substituted 7-aminocoumarins can be synthesized from readily available 7-hydroxycoumarins via alkylation with α-bromoacetamides and subsequent tandem O → N Smiles rearrangement-amide hydrolysis. The key rearrangement sequence proceeds under mild conditions to provide convenient access to various N-alkyl and N-aryl products in moderate to high yields. The process is operationally simple, inexpensive, transition-metal-free, and can be telescoped into a one-pot process.

SUBMITTER: Lippe DS

PROVIDER: S-EPMC9535735 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement.

Lippe Daniel S DS Elghawy Omar O Zucker Adam M AM Yanagawa Evan S K ESK Mathews Erin E Ahmed Yusef G YG D'Elia Paige N PN Bimson Sabrina S Walvoord Ryan R RR

ACS omega 20220921 39

N-Substituted 7-aminocoumarins can be synthesized from readily available 7-hydroxycoumarins via alkylation with α-bromoacetamides and subsequent tandem O → N Smiles rearrangement-amide hydrolysis. The key rearrangement sequence proceeds under mild conditions to provide convenient access to various N-alkyl and N-aryl products in moderate to high yields. The process is operationally simple, inexpensive, transition-metal-free, and can be telescoped into a one-pot process. ...[more]

PMID: 36211046

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