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US4304934A Synthesis of amino hydroxy cyclopentenones 失效
氨基羟基环戊烯酮的合成

Synthesis of amino hydroxy cyclopentenones
摘要:
This invention relates to a method of synthesizing 3-amino-2-hydroxy-2-cyclopentenones possessing an aliphatic substituent in the 4-position which comprises reacting cyanoacetamide with an aliphatic aldehyde to yield the corresponding .beta.-substituted-.alpha.,.alpha.'-dicyanoglutaramide, hydrolyzing the amide to the corresponding .beta.-substituted glutaric acid, esterifying the acid to the corresponding dialkyl diester, converting the diester to a 1,2-bis(trimethylsiloxy)-4-substituted cyclopentene by reductive cyclization using chlorotrimethylsilane in the presence of sodium, hydrolyzing and oxidizing the bis(trimethylsiloxy) compound to the 2-hydroxy-4-substituted-2-cyclopentenone in the presence of a cupric salt, nitrosating the 2-cyclopentenone to the 2-hydroxy-4-substituted-5-oximino-2-cyclopentenone, converting the oxime to the 2-acetoxy-3-amino-4-substituted-2-cyclopentenone by reductive acetylation and removing the acetyl group by alkanolysis to yield the 3-amino-2-hydroxy-4-substituted-2-cyclopentenone product.
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