Iron-catalyzed cyanide alkylcyanoalkyl indoline and preparation method thereof

Abstract

The invention belongs to the technical field of chemical materials, and discloses iron-catalyzed cyanoalkylcyanide alkyl indoline and a preparation method thereof. The N-allylaniline derivative exo using non-activated double bonds as a free radical receptor is selectively subjected to cyanide isopropylation and arylation reaction, so as to synthesize the 2-site substituted 3-cyanide alkylcyanoalkyl indoline with a ternary nitrile structure and without 2-position substituting by one step. The iron-catalyzed cyanide alkylcyanoalkyl indoline has the advantages that the iron-catalyzed cyanide alkylation reaction mediated by AIBN (azodiisobutyronitrile2,2-azobisisobutyronitrile) is provided for the first time; any copper salt, oxidants, alkaline or other additives are not added in the reaction;the exo selectivity is high in reaction, and the selectivity and the uncommon catalyzing activity of the iron salt are related with the metal bridging function of the iron catalyst between the free radical and the primer.

Description

technical field [0001] The invention belongs to the technical field of chemical materials, and in particular relates to an iron-catalyzed cyanoalkyl indoline and a preparation method thereof. Background technique [0002] At present, the existing technologies commonly used in the industry are as follows: [0003] In indole chemistry, the indoline structure is more difficult to synthesize than other related indole skeletons such as oxindole. There are many ways to synthesize oxindole, because it can be obtained through the derivatization reaction of isatin or other related derivatives, and can also be synthesized through the chemical synthesis of N-aryl acrylamide developed in recent years. In contrast, the construction of indoline skeletons mainly relies on the dearomatization of indole, with few methods for synthesis from acyclic starting materials. Alternatively, indolines can also be obtained by the reduction reaction of indole, but this reaction requires harsh reactio...

AI Technical Summary

Problems solved by technology

Traditionally, AIBN is only used to initiate a free radical chain reaction, and does not participate in the reaction itself, because the isobutyronitrile free radical obtained by the thermal decomposition of AIBN is too large in space and is generally considered to be unreactive.

Images