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- W1696195078 abstract "The synthesis of the decahydroquinoline ring system has been explored extensivelydue to its appearance within many biologically active natural alkaloids. New compoundscontaining such a moiety are being discovered on an ongoing basis. The present workhas sought to develop an alternative synthetic pathway to this system through the use ofDiels-Alder [4 + 2] cycloaddition chemistry.The initial focus of this research was on the development of an activated dienophilederived from 4-pyridone. Two such compounds were eventually synthesized, N-tosyl-3-formyl-5,6-dihydropyridin-4-one, and N-t-butoxycarbonyl-3-formyl-5,6-dihydropyridin-4-one. The reactivity of these compounds with several different dienes was theninvestigated in an effort to obtain the desired decahydroquinoline cycloadduct.Under inverse electron demand Diels-Alder conditions, the synthesized compoundsreacted with ethyl vinyl ether to consistently produce pyran containing bicyclic adductsunder mild conditions. The products contained a mixture of isomers in varying ratiorelative to the nitrogen substituent present.Non-activated dienes did not react with the dienophiles under normal demandconditions even with the addition of lewis acid catalysts. However, cycloadducts wereformed through reaction with the highly activated diene 1-dimethylamino-3-tertbutyldimethylsiloxy-1,3-butadiene. The products did not resemble the targetdecahydroquinoline system but instead appeared to be the result of reaction with theformyl group substituent, acting as a heterodienophile, to yield a dihydropyranone ringbridged to C-3 of the original pyridone derived dienophile." @default.
- W1696195078 created "2016-06-24" @default.
- W1696195078 creator A5026000753 @default.
- W1696195078 date "2009-01-01" @default.
- W1696195078 modified "2023-09-28" @default.
- W1696195078 title "Reactivity of substituted 4-Pyridones in normal and inverse demand Diels-Alder cycloaddition" @default.
- W1696195078 hasPublicationYear "2009" @default.
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