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One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes
Synlett ( IF 1.7 ) Pub Date : 2019-03-26 , DOI: 10.1055/s-0037-1611760
Fen Tan 1 , Zheng-Zheng Meng 1 , Xiao-Qin Xiong 1 , Guo-Ping Zeng 1 , Ming-Wu Ding 2
Affiliation  

A new, one-pot, regioselective preparation of 2,5,6,7-tetrahydroimidazo[1,2-a]imidazol-3-ones by a sequential aza-Wittig/nucleophilic addition/cyclization reaction was developed. The aza-Wittig reactions of ethyl (2Z)-3-aryl-2-[(triphenylphosphoranylidene)amino] acrylates with aryl isocyanates produced carbodiimide intermediates that were then treated sequentially with 2-aminoethanol and tosyl chloride/triethylamine to give the corresponding (2Z)-2-[(substituted)benzylidene]-2,5,6,7-tetrahydro-3H-imidazo[1,2-a]imidazol-3-ones in good overall yields and with high regioselectivity.

中文翻译:

以(乙烯基亚氨基)正膦为原料的 2,5,6,7-四氢咪唑并 [1,2-a]imidazol-3-ones 的一锅法区域选择性合成

2,5,6,7-四氢咪唑并[1,2-a]咪唑-3-酮通过连续的氮杂-Wittig/亲核加成/环化反应,开发了一种新的单锅区域选择性制备方法。(2Z)-3-芳基-2-[(三苯基亚膦基)氨基]丙烯酸乙酯与异氰酸芳基酯的氮杂-Wittig反应产生碳二亚胺中间体,然后依次用2-氨基乙醇和甲苯磺酰氯/三乙胺处理,得到相应的(2Z) )-2-[(取代的)亚苄基]-2,5,6,7-四氢-3H-咪唑并[1,2-a]咪唑-3-酮以良好的总产率和高区域选择性。
更新日期:2019-03-26
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