具有3-氮-二環[3.1.0]己烷這類型結構之化合物通常具有藥物活性或為一些具藥物活性之化合物之重要中間物,例如制菌劑、治療憂鬱症的藥物,但文獻上合成此類化合物通常需要繁雜之實驗步驟且獲得一般的產率。 本文是將1-氰基-2,3,7-三氮-二環[3.3.0]辛-2-烯類化合物(1)與乙基乙烯基酮(Ethyl Vinyl Ketone)、丙烯酸甲酯(Methyl Acrylate)、溴丙炔(3-bromoprop-1-yne)、溴化丁烷(1-bromobutane)、氯化苯(benzyl chloride ) 經親核取代(Nucleophilic substitution)或麥可加成(Michael addition)反應,形成一系列的1-氰基-2,3,7-三氮-二環[3.3.0]辛-2-烯衍生物(2)在將此ㄧ系列之1-氰基-2,3,7-三氮-二環[3.3.0]辛-2-烯衍生物在無氧的條件下進行熱裂解反應,形成一系列的1-氰基-3-氮-二環[3.1.0]己烷類化合物。 本實驗室之合成方法能以較以往文獻少的步驟成功的合成出1-氰基-3-氮-二環[3.1.0]己烷類化合物,且有不錯之產率,是合成此類化合物的新方法。
Many derivatives of 3-azabicyclo[3.1.0]hexane are reported to be biological active and useful as pharmaceuticals , By Michael addition or nucleophilic substitution, a series of 1-Cyano-2,3,7-triazabicyclo[3.3.0]oct-2-enes derivatives can be prepared. Thermolysis of these 1-Cyano-2,3,7-triazabicyclo[3.3.0]oct-2-ene derivatives , give 3-azabicyclo[3.1.0]hexane and as the major product and 4,5-dihydropyrrole or 3-cyano-4-methyl pyrrole as the minor product. This method, which can successful synthesize many derivative of 3-azabicyclo[3.1.0]hexane with few steps and in good yields, is a novel and efficient protocol to prepare derivative of 3-azabicyclo[3.1.0]hexane.