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Reaction of 2-chloroindole-3-carbaldehyde with epihalogenohydrins. Tandem oxirane-opening—1,3-oxazole-closure process |
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| Authors: | Konstantin F Suzdalev Sophia V Den’kinaValerii V Tkachev Mikhail A KiskinMikhail E Kletsky Oleg N Burov |
| Institution: | a Research Institute of Physical and Organic Chemistry of Southern Federal University, Stachki Street 194/2, 344090 Rostov-on-Don, Russian Federation b Institute of Problems of Chemical Physics, Russian Academy of Sciences, N.N. Semyonov Street 1, 142432 Czernogolovka, Moscow region, Russian Federation c N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky prosp. 31, 119991 Moscow, Russian Federation d Chemical Department of Southern Federal University, Sorge Street 7, 344090 Rostov-on-Don, Russian Federation |
| Abstract: | Reaction of 2-chloroindole-3-carbaldehyde with epibromohydrin gives the expected 1-(oxiran-2-ylmethyl) derivative. However the analogous reaction with epichlorohydrin leads to the formation of the oxazolo3,2-a]indole skeleton. Some chemical properties of this tricyclic system were investigated. Its reaction with secondary amines unexpectedly proceeds with the opening of the oxazole ring. |
| Keywords: | Indoles Aldehydes Epihalogenohydrins Oxazolo[3 2-a]indole |
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