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

Authors
Bew, SP Bull, SD Davies, SG Eames, J Baxter, AD Mykytiuk, J
Citation
Sp. Bew et al., A simple desymmetrisation approach to unsymmetric N,N '-disubstituted cyclic ureas, TETRAHEDR L, 40(39), 1999, pp. 7143-7146
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
39
Year of publication
1999
Pages
7143 - 7146
Database
ISI
SICI code
0040-4039(19990924)40:39<7143:ASDATU>2.0.ZU;2-X
Abstract
The bis-enolate derived from 1,3-di-isobutyryl-trans-4,5-tetramethylene-imi dazolidin-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 un symmetric 1-benzyl-3-methyl-trans-4,5-tetramethyleneimidazolidin-2-one 19 i n good yield. (C) 1999 Elsevier Science Ltd. All rights reserved.