A facile scheme for phthalimide ⇆ phthalimidine conversion

Frederick A. Luzzio; De Anna Piatt Zacherl; William D. Figg

doi:10.1016/S0040-4039(99)00152-5

A facile scheme for phthalimide ⇆ phthalimidine conversion

Frederick A. Luzzio^*, De Anna Piatt Zacherl, William D. Figg

^*Corresponding author for this work

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

36 Scopus citations

Abstract

Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2,2'-bipyridinium chlorochromate/m-chloroperbenzoic acid (BPCC/MCPBA) affords the original phthalimides. The reduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor.

Original language	English
Pages (from-to)	2087-2090
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(99)00152-5
State	Published - 12 Mar 1999
Externally published	Yes

Keywords

Oxidation
Protecting groups
Reduction
Sonochemistry

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10.1016/S0040-4039(99)00152-5

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title = "A facile scheme for phthalimide ⇆ phthalimidine conversion",

abstract = "Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2,2'-bipyridinium chlorochromate/m-chloroperbenzoic acid (BPCC/MCPBA) affords the original phthalimides. The reduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor.",

keywords = "Oxidation, Protecting groups, Reduction, Sonochemistry",

author = "Luzzio, {Frederick A.} and {Piatt Zacherl}, {De Anna} and Figg, {William D.}",

year = "1999",

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T1 - A facile scheme for phthalimide ⇆ phthalimidine conversion

AU - Luzzio, Frederick A.

AU - Piatt Zacherl, De Anna

AU - Figg, William D.

PY - 1999/3/12

Y1 - 1999/3/12

N2 - Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2,2'-bipyridinium chlorochromate/m-chloroperbenzoic acid (BPCC/MCPBA) affords the original phthalimides. The reduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor.

AB - Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2,2'-bipyridinium chlorochromate/m-chloroperbenzoic acid (BPCC/MCPBA) affords the original phthalimides. The reduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor.

KW - Oxidation

KW - Protecting groups

KW - Reduction

KW - Sonochemistry

UR - http://www.scopus.com/inward/record.url?scp=0033548448&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00152-5

DO - 10.1016/S0040-4039(99)00152-5

M3 - Article

AN - SCOPUS:0033548448

SN - 0040-4039

VL - 40

SP - 2087

EP - 2090

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

A facile scheme for phthalimide ⇆ phthalimidine conversion

Abstract

Keywords

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