化学学报 ›› 1963, Vol. 29 ›› Issue (6): 433-438. 上一篇    下一篇

论文

丙烯腈的化学Ⅵ.β-5,5-二取代乙内酰脲丙酰肼及其丙酮腙的合成

贾忠建, 邢其毅   

  1. 北京大学化学系
  • 投稿日期:1963-02-28 发布日期:2013-06-03

CHEMISTRY OF ACRYLONITRILE Ⅳ. SYNTHESIS OF SOME β-5, 5-DISUBSTITUED HYDANTOIN PROPIONYL HYDRAZIDES AND THEIR ACETONE HYDRAZONES

CHIA CHUNG-JIAN, HSING CHI-YI   

  1. Department of Chemistry, Peking University
  • Received:1963-02-28 Published:2013-06-03

佐藤正常最近所报告的丙烯腈和5,5-二取代乙內酰脲反应的研究,基本上和我們七年前所报告的結果相同,显然該文作者未看到我們的論文。由于某些酰肼及其腙类化合物具抗結核的作用,我們将一元及二元腈乙基取代的5,5-二取代乙內酰脲进行水解酯化,然后再进行肼解,合成一系列的酰肼。这些酰肼和丙酮縮合得到相应的腙,大部的产物均是晶体,产量約在70—90%之間。

Cyanoethylation of 5,5-disubstituted hydantoin reported by one of us (Hsing Chi-Yi) previously (1955) appears to have been overlooked by Masatsue Sato[2],whose results announced recently are essentially similar to ours.5,5-Dimethyl hydantoin can be monoor dicyanoethylated by the action of alkaline catalyst.The cyanoethylated products can be hydrolyzed by means of 2:1 hydrochloric acid or alcoholic hydrogen chloride to the corresponding acids or esters.The monocyanoethylated hydantoin was hydrolyzed by means of 60% sulphuric acid,one of the product was definitely proved to be β-amino propionic acid.Consequently the position of the cyanoethyl group is located at position 3 as assigned by Sato through other means.Tn view of the antitubercular properties of certain hydrazides and hydrazones,series of β-5,5-disubstituted hydantoin propionyl hydrazides were prepared from the corresponding esters.The hydrazides were then condensed with acetone to the hydrazones,most of the resulting products being crystalline substances,the xields ranging from 70 to 90%.