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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 34, Number 1
JKCSEZ 34(1)
February 20, 1990 

Conversion of Penicillin to Cephalosporin. The Iodination of Thiazoline-azetidinone in the Presence of Water

페니실린에서 세파로스포린으로의 전환. 물 존재하에서 티아졸린-아제티디논의 요오드화 반응
In Young Choi, Kyoo-Hyun Chung, Youn Young Lee, Yang Mo Goo

최인영, 정규현, 이윤영, 구양모
Thiazoline-azetidinone(7) 화합물은 CH2Cl2-H2O 용매에서 요오드와 반응하면 직접 3-iodo-3-methylcepham(4)을 준다. 이 반응은 상이동 촉매를 사용하면 훨씬 빨라지며 0.1당량의 요오드를 사용하면 약산성 존건하의 가수분해 반응과 비슷하게 thiazole(10)이 주생성물이었다. 고리화 반응과 가수분해 반응차이는 사용된 요오드량 및 thiazoline-azetidinone 화합물에 따라 설명될 수 있다.

The reaction of thiazoline-azetidinone (7) with I2 in CH2Cl2-H2O gave directly 3-iodo-3-methylcepham (4). A phase transfer catalyst considerably increased the reaction rate. Similar to the hydrolysis of thiazoline-azetidinone (7) under a weak acidic condition, thiazole (10) was given as major product in the treatment with 0.1 eq. of iodine. The difference between cyclization reaction and hydrolysis could be explained in terms of solvents, the amount of iodine and the nature of thiazoline-azetidinones (7).

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