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光化学方法通过环加成实现七元并六元双环[B]吲哚骨架的构建。

Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two-Carbon Ring-Expansion.

机构信息

Fakultät für Chemie und Chemische Biologie, TU Dortmund, 44227, Dortmund, Germany.

出版信息

Chemistry. 2020 Sep 16;26(52):11974-11978. doi: 10.1002/chem.202002581. Epub 2020 Aug 17.

DOI:10.1002/chem.202002581
PMID:32463529
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7540574/
Abstract

We report on the implementation of the concept of a photochemically elicited two-carbon homologation of a π-donor-π-acceptor substituted chromophore by triple-bond insertion. Implementing a phenyl connector between the slide-in module and the chromophore enabled the synthesis of cylohepta[b]indole-type building blocks by a metal-free annulative one-pot two-carbon ring expansion of the five-membered chromophore. Post-irradiative structural elaboration provided founding members of the indolo[2,3-d]tropone family of compounds. Control experiments in combination with computational chemistry on this multibond reorganization process founded the basis for a mechanistic hypothesis.

摘要

我们报告了通过三键插入实施给体-受体取代生色团的光化学引发的两碳同系化概念的实施情况。在滑动模块和生色团之间引入苯基连接器，通过无金属的五员生色团的一锅两步碳环扩展，实现了环己[b]吲哚型砌块的合成。辐照后结构的细化提供了吲哚并[2,3-d]咔唑酮类化合物的创始成员。结合多键重排过程的计算化学进行的对照实验为提出一种机制假设奠定了基础。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc1/7540574/109c270e264f/CHEM-26-11974-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc1/7540574/f9d24b7500f0/CHEM-26-11974-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc1/7540574/84a962a21dc5/CHEM-26-11974-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc1/7540574/109c270e264f/CHEM-26-11974-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc1/7540574/f9d24b7500f0/CHEM-26-11974-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc1/7540574/84a962a21dc5/CHEM-26-11974-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc1/7540574/109c270e264f/CHEM-26-11974-g003.jpg

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