Ring opening reactions of 6-oxo-substituted spiro-pyrrolidinediones: Synthesis of 4-substituted-1,5-dihydro-3-hydroxy-2-oxo-1,5-diphenyl-2H-pyrroles |
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Authors: | David W. Emerson Richard L. Titus Marlon D. Jones |
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Abstract: | Reaction of 2-oxocylalkaneglyoxylate esters with N-phenylmethyleneaniline yields spiro compounds such as 2-aza-3,4,6,-trioxo-1,2-diphenylspiro[4.4]nonane 4 and cycloalkane-2-aza-3,4,6-trioxo-1,2-diphenylspiro-[4.5]decanes 5–7 . These undergo solvolytic opening of the the oxocycloalkane ring to yield 4-substituted-1,5-dihydro-3-hydroxy-2-oxo-1,5-diphenyl-2H-pyrroles 12–17 . |
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