N,??-술피닐 비스 1,2,4-트리아졸을 이용한 에스테르와 β-락탐의 합성

Abstract

N,??-슬피닐 비스-1,2,4-트리아졸은 THF용매에서 SOCI₂,아민 및 1,2,4-트리아졸로부터 쉽게 만들어진다. 이 화합물은 카르복시산의 직접 에스테르와 축합제로, 또한 β-아미노산으로부터 β-락탐을 만드는 탈수제로 이용될 수 있었다. 이 방법을 몇가지 카르복시산과 β-아미노산에 적용시켜 보았다.

이 합성시약의 이점은 첫째 반응 후 형성되는 1,2,4-트리아졸이 중성이기 때문에 대부분의 반응이 거의 중성에서 이루어질 수 있다는 점과 둘째로 1,2,4-트리아졸이 물에 잘 녹기 때문에 일반적인 물에 의한 처리로 생성물을 정제할 수 있어서 유기합성에 흔히 사용되는 크로마토그라피에 의한 분리가 요구되지 않는다는 점이다.

N,??-Sulfinyl bis-1,2,4-triazole was conveniently prepared by the reaction of thionlyl chloride with 1,2,4-triazole. The reagent was efficient for the direct esterification of carboxylic acids and could be used as dehydrating reagent for the preparation of β-lactams form several β-amino acids.

Several noteworthy featrures of this reagent are apparent as compared with previously known reagents. First, since the 1,2,4-triazole formed as only byproduct is a neutral compound, the reactions occur normally under neutral conditions. Second, the present methods are much simpler and less laborious than the conventional methods because obtained byproduct, 1,2,4-triazole can be easily removed by the usual aqueous workup and does not required chromatographic separation in most cases.

N,??-Sulfinyl bis-1,2,4-triazole was conveniently prepared by the reaction of thionlyl chloride with 1,2,4-triazole. The reagent was efficient for the direct esterification of carboxylic acids and could be used as dehydrating reagent for the preparation of β-lactams form several β-amino acids.

Several noteworthy featrures of this reagent are apparent as compared with previously known reagents. First, since the 1,2,4-triazole formed as only byproduct is a neutral compound, the reactions occur normally under neutral conditions. Second, the present methods are much simpler and less laborious than the conventional methods because obtained byproduct, 1,2,4-triazole can be easily removed by the usual aqueous workup and does not required chromatographic separation in most cases.