A simple desymmetrisation approach to unsymmetric N,N'-disubstituted cyclic ureas

Sean P. Bew; Steven D. Bull; Stephen G. Davies; Jason Eames; Anthony D. Baxter; John Mykytiuk

doi:10.1016/S0040-4039(99)01484-7

A simple desymmetrisation approach to unsymmetric N,N'-disubstituted cyclic ureas

Sean P. Bew, Steven D. Bull, Stephen G. Davies, Jason Eames, Anthony D. Baxter, John Mykytiuk

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

2 Citations (Scopus)

Abstract

The bis-enolate derived from 1,3-di-isobutyryl-trans-4,5-tetramethylene- imidazolidin-2-one 8 is unstable and deacylates to afford dianion 11 which can be regioselectively alkylated to afford unsymmetric cyclic urea 17 in good yield. Subsequent deacylation of 17 and methylation on nitrogen affords unsymmetric 1-benzyl-3-methyltrans-4,5-tetramethyleneimidazolidin-2-one 19 in good yield.

Original language	English
Pages (from-to)	7143-7146
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4039(99)01484-7
Publication status	Published - 24 Sept 1999

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abstract = "The bis-enolate derived from 1,3-di-isobutyryl-trans-4,5-tetramethylene- imidazolidin-2-one 8 is unstable and deacylates to afford dianion 11 which can be regioselectively alkylated to afford unsymmetric cyclic urea 17 in good yield. Subsequent deacylation of 17 and methylation on nitrogen affords unsymmetric 1-benzyl-3-methyltrans-4,5-tetramethyleneimidazolidin-2-one 19 in good yield.",

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T1 - A simple desymmetrisation approach to unsymmetric N,N'-disubstituted cyclic ureas

AU - Bew, Sean P.

AU - Bull, Steven D.

AU - Davies, Stephen G.

AU - Eames, Jason

AU - Baxter, Anthony D.

AU - Mykytiuk, John

PY - 1999/9/24

Y1 - 1999/9/24

N2 - The bis-enolate derived from 1,3-di-isobutyryl-trans-4,5-tetramethylene- imidazolidin-2-one 8 is unstable and deacylates to afford dianion 11 which can be regioselectively alkylated to afford unsymmetric cyclic urea 17 in good yield. Subsequent deacylation of 17 and methylation on nitrogen affords unsymmetric 1-benzyl-3-methyltrans-4,5-tetramethyleneimidazolidin-2-one 19 in good yield.

AB - The bis-enolate derived from 1,3-di-isobutyryl-trans-4,5-tetramethylene- imidazolidin-2-one 8 is unstable and deacylates to afford dianion 11 which can be regioselectively alkylated to afford unsymmetric cyclic urea 17 in good yield. Subsequent deacylation of 17 and methylation on nitrogen affords unsymmetric 1-benzyl-3-methyltrans-4,5-tetramethyleneimidazolidin-2-one 19 in good yield.

UR - http://www.scopus.com/inward/record.url?scp=0033600882&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)01484-7

DO - 10.1016/S0040-4039(99)01484-7

M3 - Article

AN - SCOPUS:0033600882

SN - 0040-4039

VL - 40

SP - 7143

EP - 7146

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

A simple desymmetrisation approach to unsymmetric N,N'-disubstituted cyclic ureas

Abstract

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