从 Baylis-Hillman 加成物合成吲哚喹啉、吲哚吖啶和吲哚并环戊[b]喹啉：吲哚核的原位[1,3]-σ重排以获得吲哚吖啶和吲哚并环戊[b]喹啉。

Synthesis of indolylquinolines, indolylacridines, and indolylcyclopenta[b]quinolines from the Baylis-Hillman adducts: an in situ [1,3]-sigmatropic rearrangement of an indole nucleus to access indolylacridines and indolylcyclopenta[b]quinolines.

机构信息

Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei, Taiwan 116, Republic of China.

出版信息

J Org Chem. 2012 Oct 5;77(19):8451-64. doi: 10.1021/jo301313m. Epub 2012 Sep 25.

DOI:10.1021/jo301313m

PMID:22967265

Abstract

A simple and easy route to the synthesis of a variety of structurally diverse indolylquinolines, indolylacridines, and indolylcyclopenta[b]quinoline derivatives via the reductive cyclization of C-alkylated indole derivatives, derived from acyclic as well as cyclic Baylis-Hillman adducts with indoles, is described. An unusual in situ [1,3]-sigmatropic rearrangement of the indole nucleus was observed during the reductive cyclicization of α-regioselective B-H adducts containing indoles to produce indolylacridines and indolylcyclopenta[b]quinoline derivatives.

摘要

通过对非循环和环状 Baylis-Hillman 加合物与吲哚衍生的 C-烷基化吲哚衍生物的还原环化，描述了一种简单易行的方法来合成各种结构多样的吲哚喹啉、吲哚吖啶和吲哚并环戊[b]喹啉衍生物。在含有吲哚的α-区域选择性 B-H 加合物的还原环化过程中，观察到吲哚核的异常原位[1,3]-西格玛重排，生成吲哚吖啶和吲哚并环戊[b]喹啉衍生物。