CARBOXYL-PROTECTING GROUPS CONVERTIBLE INTO ACTIVATING GROUPS - CARBAMATES OF O-AMINOANILIDES ARE PRECURSORS OF REACTIVE N-ACYLUREAS

Authors
PASCAL R CHAUVEY D SOLA R
Citation
R. Pascal et al., CARBOXYL-PROTECTING GROUPS CONVERTIBLE INTO ACTIVATING GROUPS - CARBAMATES OF O-AMINOANILIDES ARE PRECURSORS OF REACTIVE N-ACYLUREAS, Tetrahedron letters, 35(34), 1994, pp. 6291-6294
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
34
Year of publication
1994
Pages
6291 - 6294
Database
ISI
SICI code
0040-4039(1994)35:34<6291:CGCIAG>2.0.ZU;2-F
Abstract
Selected carbamates of o-aminoanilides of amino acid derivatives are s table under neutral and acidic aqueous conditions but undergo a quanti tative base-catalysed intramolecular conversion into an 1-acylbenzimid azolin-2-one. The pH-rate profiles for this reaction and for the subse quent hydrolysis of the N-acylurea were established. The N-acylurea di splays a hydrolytic reactivity reaching that of active esters and is s hown to acylate leucine methyl eater.