Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 12120-12130Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02124
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Funding
- Research Fund of Ataturk University, Turkey [2015/109, FAD-2017-6107]
- Ataturk University
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The electrophilic substitution reaction of 4,7-dihydroindole with aryl-aldehydes as an electrophilic partner followed by an oxidation step to deliver 2,2'-bis(indolyl)arylmethanes was studied for the first time. The reaction afforded regioselectivity at the 2,2'-positions of indole in an operationally simple and inexpensive procedure with a variety of substrates. To the best of our knowledge, this is the first set of examples of 2,2'-bis(indolyl)arylmethanes obtained in a substituent-free manner. A facile method from dipyrromethanes to the corresponding 2-benzylindoles was also reported. In addition, 2,2'-bis(indolyl)arylmethanes were converted to 5,7-dihydroindolo[2,3-b]carbazoles.
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