化学学报 ›› 1987, Vol. 45 ›› Issue (1): 99-102. 上一篇    下一篇

研究论文

取代邻苯二酚Mannich反应研究I:

梁诚一;薛芬   

  1. 上海医科大学药学院有机化学教研室
  • 发布日期:1987-01-15

Studies on the mannich reaction of substituted catechol I:

LIANG CHENGYI;XUE FEN   

  • Published:1987-01-15

把3-[N,N-双(羧甲基)氨甲基]邻苯二酚和哌啶,吡咯,二乙胺,吗啉和哌嗪在加热可得到相应的5-取位Mannich碱.研究了Mannich反应的机理,理解了这一Mannich反应的定位是由于反应物的分子内氢键.但是在与亚胺基二乙酸反应时或3-吗啉甲基邻苯二酚与吗啉反应,得到正常的6-取代Mannich碱.

关键词: 哌啶 P, 反应机理, 红外分光光度法, 核磁共振谱法, 甲醛, 氢键, 苯二酚 P, 乙酸 P, 曼尼希反应, 吗啉

Mannich reaction of 3-[N,N-bis(carboxymethyl)aminomethyl]catechol (I) with piperidine, pyrroline, diethylamine, morpholine and piperazine gave the corresponding 5-substituted Mannich bases. The orientation of this Mannich reaction was explained through the intramol. hydrogen bonding of the starting material. However, the reaction of I with iminodiacetic acid or 3-(morpholinomethyl)catechol with morpholine gave the normal 6-substituted Mannich bases.

Key words: PIPERIDINE P, REACTION MECHANISM, INFRARED SPECTROPHOTOMETRY, NMR SPECTROMETRY, FORMALDEHYDE, HYDROGEN BONDS, BENZENEDIOL P, ACETIC ACID P, MANNICH REACTION, MORPHOLINE

中图分类号: