PRACTICAL OXIRANE RING-OPENING WITH IN-SITU PREPARED LICN - SYNTHESISOF 2-METHYL-4-(1H-1,2,4-TRIAZOL-1-YL)-1-BUTANENITRILE

Authors
TSURUOKA A NEGI S YANAGISAWA M NARA K
Citation
A. Tsuruoka et al., PRACTICAL OXIRANE RING-OPENING WITH IN-SITU PREPARED LICN - SYNTHESISOF 2-METHYL-4-(1H-1,2,4-TRIAZOL-1-YL)-1-BUTANENITRILE, Synthetic communications, 27(20), 1997, pp. 3547-3557
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
27
Issue
20
Year of publication
1997
Pages
3547 - 3557
Database
ISI
SICI code
0039-7911(1997)27:20<3547:PORWIP>2.0.ZU;2-O
Abstract
Trisubstituted oxirane 1 was regiospecifically opened with LiCN in sit u prepared from acetone cyanohydrin and LiH to provide the correspondi ng beta-hydroxy nitrile 2 in satisfactory yield, enabling us to manufa cture a key intermediate for a new antifungal agent on a multi-kg scal e. Same applications of this method to the ring opening of other oxira nes and nucleophilic substitution are also described.