A novel annulation reaction of N-substituted-2-nitrosoanilines with esters of alpha-isocyano acids. A one-pot, two-step route to 2-benzimidazole-substituted esters of alpha-amino acids

作者：Bujok Robert; Cmoch Piotr; Wrobel Zbigniew^*

来源：Tetrahedron Letters, 2014, 55(23): 3410-3413.

DOI：10.1016/j.tetlet.2014.04.030

• Heterocycles
• Nitroso group
• Isocyanides
• Cyclization

A BF3-promoted cc-addition of isocyanides to both nitrogen atoms of N-aryl-2-nitrosoanilines leads to stable BF3-complexes of 3-N-hydroxy-(2-alkylimino)benzimidazole derivatives, which, after reduction with Zn in AcOH produce 1-N-ary1-2-alkylaminobenzimidazoles. This two-step annulation proceeds efficiently in a one-pot protocol with isocyanides derived from esters of alpha-amino acids. The chirality of the latter remains unaffected in the reaction.

• 出版日期2014-6-4