Functional rearrangement of polychlorinated pyrrolidin-2-ones to 5-imino-lactams promoted by n-propylamine

C  Danieli; F  Ghelfi; A  Mucci; U M  Pagnoni; A F  Parsons; M  Pattarozzi; L  Schenetti

doi:10.1016/j.tet.2004.09.073

Functional rearrangement of polychlorinated pyrrolidin-2-ones to 5-imino-lactams promoted by n-propylamine

C Danieli, F Ghelfi, A Mucci, U M Pagnoni, A F Parsons, M Pattarozzi, L Schenetti

Chemistry

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

Abstract

The reaction of 4-methyl-pyrrolidin-2-ones, chlorinated at the C(3) and C(6) positions, with n-propylamine constitutes a new method for the preparation of 5-propylimino-pyrrolidin-2-ones or 3-pyrrolin-2-ones in generally good yields. The transformation involves a series of eliminations, substitutions and double bond shifts. This constitutes a remarkable example of a functional rearrangement. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	11493-11501
Number of pages	9
Journal	Tetrahedron
Volume	60
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2004.09.073
Publication status	Published - 6 Dec 2004

Keywords

TRANSFER RADICAL CYCLIZATION
PHOSPHORUS PENTACHLORIDE
2-IMINO 5-PYRROLIDONES
PYRROLIDONES SERIES
CUCL-TMEDA
SUCCINIMIDES
N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES
DERIVATIVES
LACTAMS
ACIDS

Access to Document

10.1016/j.tet.2004.09.073

Cite this

@article{467a3231764f4fd89ed7ed4b3438a75d,

title = "Functional rearrangement of polychlorinated pyrrolidin-2-ones to 5-imino-lactams promoted by n-propylamine",

abstract = "The reaction of 4-methyl-pyrrolidin-2-ones, chlorinated at the C(3) and C(6) positions, with n-propylamine constitutes a new method for the preparation of 5-propylimino-pyrrolidin-2-ones or 3-pyrrolin-2-ones in generally good yields. The transformation involves a series of eliminations, substitutions and double bond shifts. This constitutes a remarkable example of a functional rearrangement. (C) 2004 Elsevier Ltd. All rights reserved.",

keywords = "TRANSFER RADICAL CYCLIZATION, PHOSPHORUS PENTACHLORIDE, 2-IMINO 5-PYRROLIDONES, PYRROLIDONES SERIES, CUCL-TMEDA, SUCCINIMIDES, N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES, DERIVATIVES, LACTAMS, ACIDS",

author = "C Danieli and F Ghelfi and A Mucci and Pagnoni, {U M} and Parsons, {A F} and M Pattarozzi and L Schenetti",

year = "2004",

month = dec,

day = "6",

doi = "10.1016/j.tet.2004.09.073",

language = "English",

volume = "60",

pages = "11493--11501",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "50",

}

TY - JOUR

T1 - Functional rearrangement of polychlorinated pyrrolidin-2-ones to 5-imino-lactams promoted by n-propylamine

AU - Danieli, C

AU - Ghelfi, F

AU - Mucci, A

AU - Pagnoni, U M

AU - Parsons, A F

AU - Pattarozzi, M

AU - Schenetti, L

PY - 2004/12/6

Y1 - 2004/12/6

N2 - The reaction of 4-methyl-pyrrolidin-2-ones, chlorinated at the C(3) and C(6) positions, with n-propylamine constitutes a new method for the preparation of 5-propylimino-pyrrolidin-2-ones or 3-pyrrolin-2-ones in generally good yields. The transformation involves a series of eliminations, substitutions and double bond shifts. This constitutes a remarkable example of a functional rearrangement. (C) 2004 Elsevier Ltd. All rights reserved.

AB - The reaction of 4-methyl-pyrrolidin-2-ones, chlorinated at the C(3) and C(6) positions, with n-propylamine constitutes a new method for the preparation of 5-propylimino-pyrrolidin-2-ones or 3-pyrrolin-2-ones in generally good yields. The transformation involves a series of eliminations, substitutions and double bond shifts. This constitutes a remarkable example of a functional rearrangement. (C) 2004 Elsevier Ltd. All rights reserved.

KW - TRANSFER RADICAL CYCLIZATION

KW - PHOSPHORUS PENTACHLORIDE

KW - 2-IMINO 5-PYRROLIDONES

KW - PYRROLIDONES SERIES

KW - CUCL-TMEDA

KW - SUCCINIMIDES

KW - N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES

KW - DERIVATIVES

KW - LACTAMS

KW - ACIDS

U2 - 10.1016/j.tet.2004.09.073

DO - 10.1016/j.tet.2004.09.073

M3 - Article

VL - 60

SP - 11493

EP - 11501

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 50

ER -