Direct preparation of benzofurans from O-arylhydroxylamines.

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

doi:10.1055/s-0029-1218273

Direct preparation of benzofurans from O-arylhydroxylamines.

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

38 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.

Original language	Undefined/Unknown
Pages (from-to)	3003-3006
Number of pages	4
Journal	Synlett
Issue number	18
DOIs	https://doi.org/10.1055/s-0029-1218273
Publication status	Published - 2009

Keywords

benzofurans
O-arylhydroxylamines
hydrochlorides

Access to Document

10.1055/s-0029-1218273

Cite this

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title = "Direct preparation of benzofurans from O-arylhydroxylamines.",

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.",

keywords = "benzofurans , O-arylhydroxylamines , hydrochlorides",

author = "Fanny Contiero and Jones, \{Kevin M.\} and Matts, \{Edward A.\} and Achim Porzelle and Tomkinson, \{Nicholas C. O.\}",

year = "2009",

doi = "10.1055/s-0029-1218273",

language = "Undefined/Unknown",

pages = "3003--3006",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "18",

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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

SN - 0936-5214

SP - 3003

EP - 3006

JO - Synlett

JF - Synlett

IS - 18

ER -