Synthesis of 3-Alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones, Using a Sequential ATRC/[1,2]-Elimination, from 2,2-Dichloro-N-(2-chloroallyl)-N-RSO2-amides

Matteo Bregoli; Fulvia Felluga; Vincenzo Frenna; Franco Ghelfi; Ugo M. Pagnoni; Andrew F. Parsons; Giovanni Petrillo; Domenico Spinelli

doi:10.1055/s-0030-1258478

Synthesis of 3-Alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones, Using a Sequential ATRC/[1,2]-Elimination, from 2,2-Dichloro-N-(2-chloroallyl)-N-RSO2-amides

Matteo Bregoli, Fulvia Felluga, Vincenzo Frenna, Franco Ghelfi, Ugo M. Pagnoni, Andrew F. Parsons, Giovanni Petrillo, Domenico Spinelli

Chemistry

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

Abstract

The preparation of 3-alkyl-4-(chloromethyl)-1-RSO2-1H- pyrrol-2(5H)-ones was efficiently accomplished through a [1,2]-elimination of gamma-lactams derived from the copper(I)-catalysed ATRC of 2,2-dichloro-N-(2-chloroallyl)-N-RSO2-amides. The two reactions can be integrated into a sequential one-pot process.

Original language	English
Article number	54710SS
Pages (from-to)	1267-1278
Number of pages	12
Journal	SYNTHESIS-STUTTGART
Issue number	8
DOIs	https://doi.org/10.1055/s-0030-1258478
Publication status	Published - Apr 2011

Keywords

copper
cyclization
elimination
lactams
radical reaction
TRANSFER RADICAL CYCLIZATIONS
ATOM-TRANSFER CYCLIZATION
FORMAL TOTAL-SYNTHESIS
CHAETOMELLIC ANHYDRIDE-A
BOND-FORMING REACTIONS
GAMMA-LACTAMS
FUNCTIONAL REARRANGEMENT
AMMONIA SYNTHON
N-ALLYLTRICHLOROACETAMIDES
CATALYZED CYCLIZATION

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Bregoli, M., Felluga, F., Frenna, V., Ghelfi, F., Pagnoni, U. M., Parsons, A. F., Petrillo, G., & Spinelli, D. (2011). Synthesis of 3-Alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones, Using a Sequential ATRC/[1,2]-Elimination, from 2,2-Dichloro-N-(2-chloroallyl)-N-RSO2-amides. SYNTHESIS-STUTTGART, (8), 1267-1278. Article 54710SS. https://doi.org/10.1055/s-0030-1258478

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title = "Synthesis of 3-Alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones, Using a Sequential ATRC/[1,2]-Elimination, from 2,2-Dichloro-N-(2-chloroallyl)-N-RSO2-amides",

abstract = "The preparation of 3-alkyl-4-(chloromethyl)-1-RSO2-1H- pyrrol-2(5H)-ones was efficiently accomplished through a [1,2]-elimination of gamma-lactams derived from the copper(I)-catalysed ATRC of 2,2-dichloro-N-(2-chloroallyl)-N-RSO2-amides. The two reactions can be integrated into a sequential one-pot process.",

keywords = "copper, cyclization, elimination, lactams, radical reaction, TRANSFER RADICAL CYCLIZATIONS, ATOM-TRANSFER CYCLIZATION, FORMAL TOTAL-SYNTHESIS, CHAETOMELLIC ANHYDRIDE-A, BOND-FORMING REACTIONS, GAMMA-LACTAMS, FUNCTIONAL REARRANGEMENT, AMMONIA SYNTHON, N-ALLYLTRICHLOROACETAMIDES, CATALYZED CYCLIZATION",

author = "Matteo Bregoli and Fulvia Felluga and Vincenzo Frenna and Franco Ghelfi and Pagnoni, {Ugo M.} and Parsons, {Andrew F.} and Giovanni Petrillo and Domenico Spinelli",

year = "2011",

month = apr,

doi = "10.1055/s-0030-1258478",

language = "English",

pages = "1267--1278",

journal = "SYNTHESIS-STUTTGART",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "8",

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T1 - Synthesis of 3-Alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones, Using a Sequential ATRC/[1,2]-Elimination, from 2,2-Dichloro-N-(2-chloroallyl)-N-RSO2-amides

AU - Bregoli, Matteo

AU - Felluga, Fulvia

AU - Frenna, Vincenzo

AU - Ghelfi, Franco

AU - Pagnoni, Ugo M.

AU - Parsons, Andrew F.

AU - Petrillo, Giovanni

AU - Spinelli, Domenico

PY - 2011/4

Y1 - 2011/4

N2 - The preparation of 3-alkyl-4-(chloromethyl)-1-RSO2-1H- pyrrol-2(5H)-ones was efficiently accomplished through a [1,2]-elimination of gamma-lactams derived from the copper(I)-catalysed ATRC of 2,2-dichloro-N-(2-chloroallyl)-N-RSO2-amides. The two reactions can be integrated into a sequential one-pot process.

AB - The preparation of 3-alkyl-4-(chloromethyl)-1-RSO2-1H- pyrrol-2(5H)-ones was efficiently accomplished through a [1,2]-elimination of gamma-lactams derived from the copper(I)-catalysed ATRC of 2,2-dichloro-N-(2-chloroallyl)-N-RSO2-amides. The two reactions can be integrated into a sequential one-pot process.

KW - copper

KW - cyclization

KW - elimination

KW - lactams

KW - radical reaction

KW - TRANSFER RADICAL CYCLIZATIONS

KW - ATOM-TRANSFER CYCLIZATION

KW - FORMAL TOTAL-SYNTHESIS

KW - CHAETOMELLIC ANHYDRIDE-A

KW - BOND-FORMING REACTIONS

KW - GAMMA-LACTAMS

KW - FUNCTIONAL REARRANGEMENT

KW - AMMONIA SYNTHON

KW - N-ALLYLTRICHLOROACETAMIDES

KW - CATALYZED CYCLIZATION

UR - http://www.scopus.com/inward/record.url?scp=79953786259&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1258478

DO - 10.1055/s-0030-1258478

M3 - Article

SN - 0039-7881

SP - 1267

EP - 1278

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

IS - 8

M1 - 54710SS

ER -

Synthesis of 3-Alkyl-4-(chloromethyl)-1-RSO2-1H-pyrrol-2(5H)-ones, Using a Sequential ATRC/[1,2]-Elimination, from 2,2-Dichloro-N-(2-chloroallyl)-N-RSO2-amides

Abstract

Keywords

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