The effect of an N-substituent on the recyclization of (2-aminoaryl)bis(5-tert-butyl-2-furyl)methanes: synthesis of 3-furylindoles and triketoindoles |
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| Authors: | Alexander V. Butin Sergey K. Smirnov |
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| Affiliation: | a Research Institute of Heterocyclic Compounds Chemistry, Kuban State University of Technology, Moskovskaya St. 2, Krasnodar 350072, Russian Federation
b Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119992, Russian Federation |
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| Abstract: | The recyclization of (2-aminophenyl)bis(5-tert-butyl-2-furyl)methane derivatives has been studied. It was shown that the acid-catalyzed recyclization of N-tosylamides leads to the formation of 2-(3-oxoalkyl)-3-(2-furyl)indoles. In contrast, under the same reaction conditions, acetamides are transformed into indoles containing three keto groups. The acid-catalyzed removal of the acetyl group from these substrates facilitated protolytic furan ring opening. The same triketones can be directly obtained from (2-aminoaryl)bis(5-tert-butyl-2-furyl)methanes. |
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| Keywords: | Furan Recyclization Indole 1,4-Diketone |
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