Tetrahedron p. 6319 - 6328 (1998)
Update date:2022-09-26
Topics:
Xu, Yuelian
Dolbier Jr., William R.
Synthetic utility of the novel difluoro ketene aminal 1 was extended to the preparation of a number of potentially biologically-interesting difluoro barbituric acid derivatives via initial hetero-Diels-Alder reactions of 1 with p-substituted-5-benzylidene-1,3-dimethylbarbituric acids 3. These cycloadducts 4 upon hydrolysis, provided the formal Michael addition product amides 5 which were readily converted to the respective carboxylic acids 6. The acids were dehydratively cyclized to form novel bicyclic lactones 8.
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Doi:10.1002/aoc.1728
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