化学学报 ›› 1964, Vol. 30 ›› Issue (2): 183-192. 上一篇    下一篇

论文

1, 2, 4-三嗪类化合物的研究Ⅲ.3, 5-取代-1, 2, 4-三嗪-6-羧酸及其衍生物

王序, 蔡孟深, 何颖镛, 李际和   

  1. 北京医学院药学系
  • 投稿日期:1963-06-22 发布日期:2013-06-03

CHEMISTRY OF 1, 2, 4-TRIAZINES Ⅲ. 3,5-DISUBSTITUTED-1, 2, 4-TRIAZINE-6-CARBOXYLIC ACIDS AND THEIR DERIVATIVES

WANG HSIU(HSIU WANG), TSAI MENG-SHENG, HO YING-YUNG AND LI CHI-HO   

  1. Department of Pharmacy, Peking Medical College
  • Received:1963-06-22 Published:2013-06-03

本文报告3,5-取代-1,2,4-三嗪-6-羧酸及其衍生物的制备和性质.3-巯酮基-5-羰基-或3,5-二羰基-2,3,4,5-四氢-1,2,4-三嗪-6-羧酸乙酯与氨水及水合肼作用,能分别获在水内稳定的相应酰胺的铵盐及酰肼的肼盐.这些化合物比相应取代嘧啶的酸性增加很多,但类似的3,5-取代-2,3,4,5-四氢-1,2,4-三嗪及6-甲基衍生物不能与氨水成盐,说明6-羧基有增强酸性的作用.3-甲硫基-5-羰基-2,5-二氢-1,2,4-三嗪-6-羧酸乙酯室温与氨水作用得到其相应的酰胺,如在封管中加热至120°,则部分产物的3-甲硫基水解为羟基,得3,5-二羰基-2,3,4,5-四氢-1,2,4-三嗪-6-羧酸酰胺;与当量之水合肼作用得其相应的酰肼,如与过量水合肼作用,则3-甲硫基也被肼基置换.这些3-甲硫基衍生物均不与氨或肼成盐,说明硫经烷基化后,化合物酸性降低.曾研究1,2,4-三嗪环对6-羧酸衍生物性质及6-位取代基对环性质的影响.3,5-取代-2,3,4,5-四氢-1,2,4-三嗪-6-羧酸酰胺在无水乙醇中回馏下通入干燥氯化氢,酰胺基不变为乙酯,而水解为羧基.当3-甲硫基存在时,甲硫基被羧基置换;如6-位为甲基取代,则3-甲硫基-的水解速度显著减慢.本文尚报告这些化合物在四种溶剂系统中的纸层析结果,及部分化合物的红外吸收光谱.并根据红外光谱讨论其结构.

The preparations and properties of some 3,5-disubstituted-1,2,4-triazine-6-carboxylic acids and their derivatives were reported.Ethyl 3-thiono-5-oxo- or 3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylate reacted with aqueous ammonia or with hydrazine hydrate to give stable ammonium salts of the corresponding amides or the hydrazine salts of the corresponding hydrazides.But 3-thiono-5-oxo- or 3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazines and their 6-methyl derivatives could not form salts with ammonia.