Acta Chimica Sinica ›› 1956, Vol. 22 ›› Issue (6): 513-523. Previous Articles     Next Articles

氮大圜化合物的合成——Ⅱ.1-甲基氮七圜与1-甲基氮八圜的衍生物

陆启荣1,2, F. F. Blicke1,2   

  1. 1. 广州中山大学化学系;
    2. 密歇根大学药学系
  • 投稿日期:1956-08-06 发布日期:2013-06-03

SYNTHESIS OF LARGE-MEMBERED NITROGENOUS RING COMPOUNDS——Ⅱ.DERIVATIVES OF 1-METHYLHEXAMETHYLENIMINE AND 1-METHYLHEPTAMETHYLENIMINE

LU CHI-JUNG1,2, F. F. BLICKE1,2   

  1. 1. Department of Chemistry, Sun Yat-Sen University;
    2. College of Pharmacy, University of Michigan
  • Received:1956-08-06 Published:2013-06-03

1. Cyclohexanone was condensed with diethyloxalate to form ethyl 2-ketocyclohexylglyoxylate. This substance lost carbon monoxide, when heated with a mixture of powdered glass and powdered iron, to form 2-carbethoxycyclohexanone. The ester was treated with sodium azide and sulfuric acid (Schmidt reaction).in chloroform solution, and was thereby converted into 2-carbethoxy-7-ketohexamethylenimine. The lactam u}as hydrolyzed to alpha-aminopimelic acid, a known substance, which had been obtained previously by Shecter and Kirk, who hydrolyzed 7-cyano-2-ketohexamethylenimine.