Highly efficient methods for metacyclophane synthesis |
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Authors: | Masayuki Sato Tsunehisa OdaKen-ichi Iwamoto Emi Murakami |
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Affiliation: | School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan |
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Abstract: | Highly efficient methods for synthesizing metacyclophanes such as 2,6-bridged pyrones and pyridines are described. 4-Hydroxy-2-pyrone derivative 3 bridged at the 3 and 6-positions is readily available. This compound was transformed into 2,6-bridged 4-pyrone 4 on heating in ethanol or in hydrochloric acid. Heating 4 with ammonia or methylamine afforded the corresponding 2,6-bridged 4-pyrone 7 or 8. These pyridones were synthesized directly from 3 by treatment with ammonia or methylamine. These methods have a wide applicability to the bridge length of metacyclophane; compounds with a short bridge (n=8) as well as long bridge (n=18) are synthesized in satisfactory yields. |
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Keywords: | metacyclophane pyridones methylamine |
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