Synthesis of new triazole substituted pyroaminoadipic and pipecolic acid derivatives

详细信息    查看全文

• 作者：Lenda ; Fatimazohra ; Guenoun ; Farhate ; Tazi ; Bouchra ; Ben larbi ; Najib ; Martinez ; Jean ; Lamaty ; Fr??d??ric
• 刊名：Tetrahedron Letters
• 出版年：2004
• 出版时间：November 22, 2004
• 年：2004
• 卷：45
• 期：48
• 页码：8905-8907
• 全文大小：255 K

文摘

Racemic 5-(4,5-substituted-1H-1,2,3-triazol-1yl)-pyroaminoadipic and pipecolic acid derivatives were synthesized from meso dimethyl-??,?????-dibromoadipate 1 in good yields using mild reaction conditions. The key step of this reaction sequence was the 1,3-dipolar cycloaddition of an acetylenic compound on ??-azido-?????-bromoadipate 2. A reactive ??-(substituted-1H-1,2,3-triazol-1-yl)-?????- bromoadipate derivative 3a???d was generated and reacted with sodium azide followed by Pd/C-catalyzed hydrogenation to provide lactams 5a???d. The chemoselective reduction of the amide carbonyl group of 5a???d with BH₃ followed by acid hydrolysis provided 5-(4,5-substituted-1H-1,2,3-triazol-1-yl) pipecolic acids in racemic form.