An improved protocol for the preparation of 5, 11-dialkyl-6, 12-di(hetero)aryl-5, 11-dihydroindolo[3, 2-b]carbazoles and synthesis of their new 2, 8-dicyano-/2, 8-bis(benzo[d]thiazol-2-yl)-substituted derivatives(Article)(Open Access)
- aPostovsky Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, Ekaterinburg, 620990, Russian Federation
- bUral Federal University Named after the First President of Russia, B. N. Yeltsin, Ekaterinburg, 620002, Russian Federation
Abstract
A number of 5, 11-dialkyl-6, 12-di(hetero)aryl-5, 11-dyhydroindolo[3, 2-b]carbazoles has been synthesized by modified method based on HBr catalyzed condensation of (hetero)aromatic aldehydes with indole in MeCN solution affording 5, 6, 11, 12-tetrahydroindolo[3, 2-b]carbazoles, that have been aromatized with I2 in DMF solution for 1 h at reflux, followed by alkylation of 5, 11-dihydro compounds. New 2, 8-dicyano-(10 examples) as well as 2, 8-bis(benzo[d]thiazol-2-yl)-substituted (5 examples) derivatives of these 5, 11-dyhydroindolo[3, 2-b]carbazoles have been obtained through their initial C2, 8-formylation, followed by treatment of dialdehydes with excess of hydroxylamine and dehydration of the formed aldoximes with acetic anhydride or by interaction with excess of 2-aminothiophenol in DMSO solution, respectively. © 2018 Arkat. All rights reserved.
Funding details
| Funding sponsor | Funding number | Acronym |
|---|---|---|
| Russian Science Foundation | 16-13-10435 | RSF |
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This research study was supported financially by the Russian Science Foundation (Project No. 16-13-10435).
- ISSN: 15517004
- CODEN: AGFUA
- Source Type: Journal
- Original language: English
- DOI: 10.24820/ark.5550190.p010.557
- Document Type: Article
- Publisher: Arkat
Irgashev, R.A.; Postovsky Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, Ekaterinburg, Russian Federation;
© Copyright 2018 Elsevier B.V., All rights reserved.
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