One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes

One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes
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以(乙烯基亚氨基)正膦为原料，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

DOI：
10.1055/s-0037-1611760
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发表时间：
2019-03
期刊：
Synlett
影响因子：
2
通讯作者：
Ding Ming-Wu
Ding Ming-Wu
中科院分区：
化学4区
文献类型：
--
作者：
Tan Fen;Meng Zheng-Zheng;Xiong Xiao-Qin;Zeng Guo-Ping;Ding Ming-Wu

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摘要提出了一种新的、一锅法、区域选择性地通过氮杂-Wittig/亲核加成/环合反应合成2，5，6，7-四氢咪唑并[1，2-a]咪唑-3-酮的方法。（2 Z）-3-芳基-2-[（三苯基膦基）氨基]丙烯酸乙酯与芳基异氰酸酯的氮杂-Wittig反应生成碳二亚胺中间体，然后依次用2-氨基乙醇和对甲苯磺酰氯/三乙胺处理，以良好的总产率和高的区域选择性得到相应的（2 Z）-2-[（取代）亚苄基]-2，5，6，7-四氢-3H-咪唑并[1，2-a]咪唑-3-酮。
Abstract 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.
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