Controlling the regioselectivity of the ring opening of spiro-epoxyoxindoles for efficient synthesis of C(3)-N(1')-bisindoles and C(3)-N(1')-diindolylmethane
| Autor: | Sayan Roy, Saumen Hajra, Subrata Maity, Dhiraj Das |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Indole test
010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Regioselectivity Diindolylmethane 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound Nucleophile Indoline SN2 reaction Physical and Theoretical Chemistry |
| Zdroj: | Organicbiomolecular chemistry. 17(33) |
| ISSN: | 1477-0539 |
| Popis: | An efficient strategy for the construction of both C(3)–N(1′) bisindoles and C(3)–N(1′) diindolylmethane has been explored via proper tuning of the nucleophilicity of indoline/indole to spiro-epoxyoxindole. Lewis acid-catalyzed highly regio- as well as chemoselective coupling at the C-3 centre of spiro-epoxyoxindoles with indolines furnishes C(3)–N(1′) bisindoles whereas base mediated and Lewis acid-catalyzed regioselective coupling at the less hindered site of spiro-epoyoxindoles with indoles via the SN2 mechanism provides C(3)–N(1′) diindolylmethane. |
| Databáze: | OpenAIRE |
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