Direct preparation of benzofurans from O-arylhydroxylamines.

Fanny Contiero, Kevin M. Jones, Edward A. Matts, Achim Porzelle, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran deriv. via a proposed one-pot condensation-rearrangement-cyclization reaction sequence in good to excellent yields. E.g., in the presence of methanesulfonic acid, reaction of H2NOPh.HCl and cyclohexanone gave 70% benzofuran deriv. I.
LanguageUndefined/Unknown
Pages3003-3006
Number of pages4
JournalSynlett
Issue number18
DOIs
Publication statusPublished - 2009

Keywords

  • benzofurans
  • O-arylhydroxylamines
  • hydrochlorides

Cite this

Contiero, Fanny ; Jones, Kevin M. ; Matts, Edward A. ; Porzelle, Achim ; Tomkinson, Nicholas C. O. / Direct preparation of benzofurans from O-arylhydroxylamines. In: Synlett. 2009 ; No. 18. pp. 3003-3006.
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Direct preparation of benzofurans from O-arylhydroxylamines. / Contiero, Fanny; Jones, Kevin M.; Matts, Edward A.; Porzelle, Achim; Tomkinson, Nicholas C. O.

In: Synlett, No. 18, 2009, p. 3003-3006.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Direct preparation of benzofurans from O-arylhydroxylamines.

AU - Contiero, Fanny

AU - Jones, Kevin M.

AU - Matts, Edward A.

AU - Porzelle, Achim

AU - Tomkinson, Nicholas C. O.

PY - 2009

Y1 - 2009

N2 - Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran deriv. via a proposed one-pot condensation-rearrangement-cyclization reaction sequence in good to excellent yields. E.g., in the presence of methanesulfonic acid, reaction of H2NOPh.HCl and cyclohexanone gave 70% benzofuran deriv. I.

AB - Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran deriv. via a proposed one-pot condensation-rearrangement-cyclization reaction sequence in good to excellent yields. E.g., in the presence of methanesulfonic acid, reaction of H2NOPh.HCl and cyclohexanone gave 70% benzofuran deriv. I.

KW - benzofurans

KW - O-arylhydroxylamines

KW - hydrochlorides

U2 - 10.1055/s-0029-1218273

DO - 10.1055/s-0029-1218273

M3 - Article

SP - 3003

EP - 3006

JO - Synlett

T2 - Synlett

JF - Synlett

SN - 0936-5214

IS - 18

ER -