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- Title
Synthesis of tetracyclic system of 2,4-di( tert-butyl)-6,7-dihydrofuro[2′,3′:3,4]cyclohepta[1,2- b]indole.
- Authors
Butin, Alexander V.; Kostyukova, Olga N.; Tsiunchik, Fatima A.; Uchuskin, Maxim G.; Serdyuk, Olga V.; Trushkov, Igor V.
- Abstract
For the first time, tetracyclic compounds, namely, furo[2′,3′:3,4]cyclohepta[1,2-b]indoles were synthesized by recyclization of ortho-substituted aryldifurylmethanes containing tert-butyl groups at C5 positions of the furan rings. It was shown that [2-(benzoylamino)phenyl]bis(5- tert-butyl-2-furyl)methanes are transformed into tetracycles at room temperature under treatment with POCl in benzene solution containing some drops of water. The reaction proceeds via the intermediate formation of 1-benzoylamino-3-(5- tert-butyl-2-furyl)-2-(4,4-dimethyl-3-oxopentyl)indoles which can be isolated from the reaction mixture. The method is very simple but its application is restricted due to side reactions if electron-releasing groups are present in . On the other hand, the decrease of electron density on furan ring in the starting compounds (for example, the use of [2-X-phenyl]difurylmethanes (where X = tosylamino or hydroxy group) prevents cyclization under the studied reaction conditions. As a result, corresponding ketones are formed as products of recyclization. J. Heterocyclic Chem., (2011).
- Subjects
KETONES; INDOLE; BENZENE; IONOSPHERIC electron density; BENZOFURAN; FURANS; ORGANIC synthesis
- Publication
Journal of Heterocyclic Chemistry, 2011, Vol 48, Issue 3, p684
- ISSN
0022-152X
- Publication type
Article
- DOI
10.1002/jhet.635