期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 3, 页码 1154-1161出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02257
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资金
- DST
- Department of Biotechnology (DBT)
- World Academy of Sciences (TWAS)
- UGC, New Delhi
- CSIR, New Delhi
- University of Delhi
A facile synthesis of highly functionalized spirobutenolides was carried out by a nitroalkane carbanion-induced ring opening and relactonization via a denitration reaction of 2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles and 2-oxo-2,5-dihydrothiochromeno [4,3-b]pyran-3-carbonitriles. However, when nitroethane was used as a nucleophile source in lieu of nitromethane, a mixture of (E)- and (Z)-isomers of the corresponding spirobutenolides was obtained in a different ratio. The structure and geometry of the product were confirmed by single-crystal X-ray diffraction. The isolated (E)- and (Z)-butenolides with the treatment with sodium ethoxide in DMF at room temperature provided highly substituted trienes via an allylic ring opening followed by decarboxylation.
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