Arylation Using Sulfonamides: Phenylacetamide Synthesis through Tandem Acylation–Smiles Rearrangement

Helen L. Barlow; Pauline T. G. Rabet; Alastair Durie; Tim Evans; Michael F. Greaney

doi:10.1021/acs.orglett.9b03429

Arylation Using Sulfonamides: Phenylacetamide Synthesis through Tandem Acylation–Smiles Rearrangement

Helen L. Barlow, Pauline T. G. Rabet, Alastair Durie, Tim Evans, Michael F. Greaney

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

205 Downloads (Pure)

Abstract

A range of electron-poor and heterocyclic sulfonamides react with phenylacetyl chlorides to produce benzhydryl derivatives in a single step. The reaction proceeds via tandem amide bond formation/Dohmori–Smiles rearrangement under the simple conditions of an aqueous base. In the case of o-nosylamides, a further reaction takes place at the nitro group to yield indazoles

Original language	English
Pages (from-to)	9033-9035
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.9b03429
Publication status	Published - 1 Nov 2019

Access to Document

10.1021/acs.orglett.9b03429

final_manuscript 25 10 2019 (002)Accepted author manuscript, 430 KB

https://pubs.acs.org/doi/10.1021/acs.orglett.9b03429

Cite this

@article{98a7785269334af0939dfaa51660bde8,

title = "Arylation Using Sulfonamides: Phenylacetamide Synthesis through Tandem Acylation–Smiles Rearrangement",

abstract = "A range of electron-poor and heterocyclic sulfonamides react with phenylacetyl chlorides to produce benzhydryl derivatives in a single step. The reaction proceeds via tandem amide bond formation/Dohmori–Smiles rearrangement under the simple conditions of an aqueous base. In the case of o-nosylamides, a further reaction takes place at the nitro group to yield indazoles",

author = "Barlow, {Helen L.} and Rabet, {Pauline T. G.} and Alastair Durie and Tim Evans and Greaney, {Michael F.}",

year = "2019",

month = nov,

day = "1",

doi = "10.1021/acs.orglett.9b03429",

language = "English",

pages = "9033--9035",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Arylation Using Sulfonamides: Phenylacetamide Synthesis through Tandem Acylation–Smiles Rearrangement

AU - Barlow, Helen L.

AU - Rabet, Pauline T. G.

AU - Durie, Alastair

AU - Evans, Tim

AU - Greaney, Michael F.

PY - 2019/11/1

Y1 - 2019/11/1

N2 - A range of electron-poor and heterocyclic sulfonamides react with phenylacetyl chlorides to produce benzhydryl derivatives in a single step. The reaction proceeds via tandem amide bond formation/Dohmori–Smiles rearrangement under the simple conditions of an aqueous base. In the case of o-nosylamides, a further reaction takes place at the nitro group to yield indazoles

AB - A range of electron-poor and heterocyclic sulfonamides react with phenylacetyl chlorides to produce benzhydryl derivatives in a single step. The reaction proceeds via tandem amide bond formation/Dohmori–Smiles rearrangement under the simple conditions of an aqueous base. In the case of o-nosylamides, a further reaction takes place at the nitro group to yield indazoles

U2 - 10.1021/acs.orglett.9b03429

DO - 10.1021/acs.orglett.9b03429

M3 - Letter

SN - 1523-7060

SP - 9033

EP - 9035

JO - Organic Letters

JF - Organic Letters

ER -

Arylation Using Sulfonamides: Phenylacetamide Synthesis through Tandem Acylation–Smiles Rearrangement

Abstract

Access to Document

Fingerprint

Cite this