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参与生物化学和光电子学研究：酰基乙炔基环烷[]吡咯与 Δ-吡咯啉通过[3+2]环加成反应构建吡咯并[1',2':2,3]咪唑并[1,5-]吲哚和环庚[4,5]吡咯并[1,2-]吡咯并[1,2-]咪唑。

Contributing to Biochemistry and Optoelectronics: Pyrrolo[1',2':2,3]imidazo[1,5-]indoles and Cyclohepta[4,5]pyrrolo[1,2-]pyrrolo[1,2-]imidazoles via [3+2] Annulation of Acylethynylcycloalka[]pyrroles with Δ-Pyrrolines.

机构信息

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia.

出版信息

Int J Mol Sci. 2023 Feb 8;24(4):3404. doi: 10.3390/ijms24043404.

DOI:10.3390/ijms24043404
PMID:36834813
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9959468/
Abstract

Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[]indolyl moieties, acylethynylcycloalka[]pyrroles, are readily annulated with Δ-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1',2':2,3]imidazo[1,5-]indoles and cyclohepta[4,5]pyrrolo[1,2-]pyrrolo[1,2-]imidazoles functionalized with an acylethenyl group in up to an 81% yield. This original synthetic approach contributes to the arsenal of chemical methods promoting drug discovery. Photophysical studies show that some of the synthesized compounds, e.g., benzo[]pyrroloimidazoindoles, are prospective candidates for TADF emitters of OLED.

摘要

具有四氢吲哚基、环烷并吡咯基和二氢苯并[]吲哚基部分的可用吡咯烷基炔酮、酰基乙炔基环烷[]吡咯，可与Δ-吡咯烷（MeCN/THF，70°C，8 小时）容易环合，得到一系列新型吡咯并[1'，2':2,3]咪唑[1,5-]吲哚和环庚[4,5]吡咯并[1,2-]吡咯并[1,2-]咪唑，产率高达 81%。这种新颖的合成方法为药物发现提供了化学方法的新途径。光物理研究表明，一些合成的化合物，例如苯并[]吡咯并咪唑吲哚，是 OLED 中 TADF 发射器的有前途的候选物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/94ea9da4f2e7/ijms-24-03404-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/358edc48b3b3/ijms-24-03404-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/2469da38f5a8/ijms-24-03404-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/6f54666614a6/ijms-24-03404-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/771ca8d44e75/ijms-24-03404-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/f90748ec9d64/ijms-24-03404-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/513ae77ac5ca/ijms-24-03404-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/94ea9da4f2e7/ijms-24-03404-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/358edc48b3b3/ijms-24-03404-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/2469da38f5a8/ijms-24-03404-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/6f54666614a6/ijms-24-03404-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/771ca8d44e75/ijms-24-03404-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/f90748ec9d64/ijms-24-03404-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/513ae77ac5ca/ijms-24-03404-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f907/9959468/94ea9da4f2e7/ijms-24-03404-g002.jpg

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