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通过费歇尔吲哚化反应构建具有并噻吩和吡咯环的杂并芳烃。

Construction of Heteroacenes with Fused Thiophene and Pyrrole Rings via the Fischer Indolization Reaction.

机构信息

Postovsky Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences , Ekaterinburg 620990, Russia.

Ural Federal University named after the First President of Russia, B.N. Yeltsin , Ekaterinburg 620002, Russia.

出版信息

Org Lett. 2016 Feb 19;18(4):804-7. doi: 10.1021/acs.orglett.6b00081. Epub 2016 Feb 3.

DOI:10.1021/acs.orglett.6b00081
PMID:26841237
Abstract

A convenient approach to ladder-type 6H-benzo[4',5']thieno[2',3':4,5]thieno[3,2-b]indoles bearing various substituents in both terminal benzene rings has been developed. The protocol suggested for preparing these N,S-heteroacenes is based on using easily available reagents, such as cinnamic acids and arylhydrazines, which can be involved in the Fischer indole synthesis, as the key step. A similar condensed system of 12H-benzo[4″,5″]thieno[2″,3″:4',5']thieno[2',3':4,5]thieno[3,2-b]indole, bearing six rings, has also been obtained.

摘要

一种方便的方法被开发出来,用于合成具有各种取代基的 ladder-type 6H-benzo[4',5']thieno[2',3':4,5]thieno[3,2-b]indoles,这些取代基位于两个末端苯环上。用于制备这些 N,S-杂芳烃的方案基于使用容易获得的试剂,如肉桂酸和芳基肼,它们可以作为关键步骤参与 Fischer 吲哚合成。类似的 12H-benzo[4″,5″]thieno[2″,3″:4',5']thieno[2',3':4,5]thieno[3,2-b]indole 稠合体系,也含有六个环,也已经得到了。

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引用本文的文献

1
An Approach to the Construction of Benzofuran-thieno[3,2-]indole-Cored N,O,S-Heteroacenes Using Fischer Indolization.一种利用费歇尔吲哚合成法构建苯并呋喃并噻吩并[3,2-]吲哚为核心的N,O,S-杂蒽的方法。
ACS Omega. 2021 Nov 15;6(47):32277-32284. doi: 10.1021/acsomega.1c05239. eCollection 2021 Nov 30.
2
Benzo[]selenophene/thieno[3,2-]indole-Based N,S,Se-Heteroacenes for Hole-Transporting Layers.用于空穴传输层的基于苯并[]硒吩/噻吩并[3,2-]吲哚的N,S,Se-杂并苯
ACS Omega. 2020 Apr 17;5(16):9377-9383. doi: 10.1021/acsomega.0c00383. eCollection 2020 Apr 28.
3
Synthesis of aryl-substituted thieno[3,2-]thiophene derivatives and their use for N,S-heterotetracene construction.
芳基取代的噻吩并[3,2-]噻吩衍生物的合成及其在N,S-杂四并苯构建中的应用。
Beilstein J Org Chem. 2019 Nov 12;15:2678-2683. doi: 10.3762/bjoc.15.261. eCollection 2019.