Synthesis and Selected Transformations of 1H-Imidazole 3-Oxides Derived from Amino Acid Esters

✍ Scribed by Marcin Jasiński; Grzegorz Mlostoń; Anthony Linden; Heinz Heimgartner

• Book ID: 102259876
• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 397 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890205

✦ Synopsis

Abstract

A series of new optically active 1__H__‐imidazole 3‐oxides 5 with a substituted acetate group at N(1) as the chiral unit were prepared by the reaction of α‐(hydroxyimino) ketones, α‐amino acid methyl esters, and formaldehyde. In an analogous reaction, ethyl 2‐(hydroxyimino)‐3‐oxobutyrate and 1,3,5‐trialkylhexahydro‐1,3,5‐triazines gave 3‐oxido‐1__H__‐imidazole‐4‐carboxylates 14, which easily rearranged into the 2‐oxo derivatives 15. Selected examples of N‐oxides 5 could be transformed into the corresponding 2,3‐dihydro‐1__H__‐imidazole‐2‐thione derivatives 10 via a ‘sulfur‐transfer reaction’, and the reduction of the histidine derivative 5i with Raney‐Ni yielded the optically active 2,3‐bis(imidazolyl)propanoate 12. Furthermore, reaction of the (1__H__‐imidazol‐1‐yl)acetates with primary amines yielded the corresponding acetamides.