Preparation of methano[1,3]oxazolo[3,2-a]quinolin-2-ones from 2-(pent-3-en-2-yl)anilines |
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Authors: | G. G. Mazgarova A. A. Fatykhov R. R. Gataullin |
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Affiliation: | 1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Russia
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Abstract: | Acid-catalyzed Claisen aromatic rearrangement of ethyl N-(pent-3-en-2-yl)-N-phenylglycinate leads to the formation of ethyl N-[2-(pent-3-en-2-yl)phenyl]glycinate. The reaction of sodium salt of N-acetyl-2-(pent-3-en-2-yl)-4-methylaniline with methyl bromoacetate afforded ethyl N-acetyl-N-[4-methyl-2-(pent-3-en-2-yl)phenyl]glycinate. The hydrolysis of synthesized esters, the conversion of the obtained acids by treating with ethyl chloroformate into munchnones, and the subsequent [3+2]-cycloaddition provided methoxazoloquinoline structures. |
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