Transformations of 1-(Oxiranylmethyl)-1,2,3-triazoles into 2-(Oxiranylmethyl)-1,2,3-triazoles and Alkanenitriles
Transformations of 1-(Oxiranylmethyl)-1,2,3-triazoles into 2-(Oxiranylmethyl)-1,2,3-triazoles and Alkanenitriles
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1-(环氧乙烷基甲基)-1,2,3-三唑转化为2-(环氧乙烷基甲基)-1,2,3-三唑和烷腈
DOI：
10.1055/s-0032-1317937
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发表时间：
2013
期刊：
影响因子：
2
通讯作者：
Keiji Tanino
中科院分区：
文献类型：
--
作者：
Kosuke Namba;Ayumi Osawa;Akane Mera;Keiji Tanino
建立了 1-(环氧乙烷基甲基)-1,2,3-三唑转化为 2-(环氧乙烷基甲基)-1,2,3-三唑或烷腈的新反应。用三氟甲磺酸和t-BuOH连续处理底物得到4,6-二氢-5-羟基-1,3a,6a-三氮杂戊二烯衍生物。在NaH的影响下，双环化合物转化为2-(环氧乙烷基甲基)-1,2,3-三唑或烷腈。反应途径取决于环氧化物侧链的取代基模式。
New reactions for the transformation of 1-(oxiranylmethyl)-1,2,3-triazoles into 2-(oxiranylmethyl)-1,2,3-triazoles or alkanenitriles were established. Successive treatment of the substrate with triflic acid andt-BuOH afforded 4,6-dihydro-5-hydroxy-1,3a,6a-triazapentalene derivative. Under the influence of NaH, the bicyclic compound was converted into a 2-(oxiranylmethyl)-1,2,3-triazole or an alkanenitrile. The reaction pathway depends on the substituent pattern of the epoxide side chain.