3-氮杂-1,5-烯炔的环化和 N-碘代琥珀酰亚胺诱导的亲电碘环化反应合成 1,2-二氢吡啶和 3-碘-1,2-二氢吡啶。

Cyclization and N-iodosuccinimide-induced electrophilic iodocyclization of 3-aza-1,5-enynes to synthesize 1,2-dihydropyridines and 3-iodo-1,2-dihydropyridines.

机构信息

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China.

出版信息

J Org Chem. 2013 Apr 19;78(8):4065-74. doi: 10.1021/jo400387b. Epub 2013 Mar 26.

Abstract

Metal-free cyclization and N-iodosuccinimide-induced electrophilic iodocyclization of readily available 3-aza-1,5-enynes have been developed. The reactions selectively give 1,2-dihydropyridines and 3-iodo-1,2-dihydropyridines involving an aza-Claisen rearrangement and a 6π-electrocyclization step. Furthermore, the reaction could be carried out in 10 g scale for the synthesis of 1,2-dihydropyridines.

摘要

发展了一种无金属的环化反应和 N-碘代琥珀酰亚胺诱导的易得的 3-氮杂-1,5-烯炔的亲电碘环化反应。这些反应选择性地生成了 1,2-二氢吡啶和 3-碘-1,2-二氢吡啶，涉及氮杂-Claisen 重排和 6π-电环化步骤。此外，该反应可以在 10 克规模下进行，用于合成 1,2-二氢吡啶。