1,4-Rearrangement of 7-(2-acetamido-2,3-dideoxyhex-2-enopyranosyl)theophylline derivatives |
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Authors: | Nevenka Pravdić |
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Affiliation: | Department of Organic Chemistry and Biochemistry, Rudjer Bo?kovi? Institute, 41001 Zagreb, Croatia Yugoslavia |
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Abstract: | Treatment of 7-2(-acetamido-2,3-dideoxyhex-2-enopyranosyl)theophylline derivatives with boron trifluoride etherate in boiling methanol led to the isolation of 7-(methyl 2-acetamido-2,3,4-trideoxyhex-2-enopyranosid-4-yl)theophylline derivatives. Some mechanistic features of this 1,4-rearrangement followed by solvolysis are discussed, and a rationalization of the formation of the C-4′ derivatives in the fusion reaction of 2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-d-arabino-hex-l-enitol with theophylline is offered. |
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