- Synthesis of N-Substituted 4-(2-Oxoalkyl)-1,4-dihydronicotinates and Their Inverse Electron Demand Diels-Alder Reaction with 3,4-Dichlorothiophene 1,1-Dioxide
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N-Substituted 4-(2-oxoalkyl)-1,4-dihydronicotinates 4 were prepared in high yields by the reaction of quaternized nicotinium salts with silyl enol ethers.These 1,4-dihydronicotinates acted as dienophiles in Diels-Alder reactions with the electron-deficient 3,4-dichlorothiophene 1,1-dioxide.The cycloaddition proceeded regio- and stereoselectively in good yield to give 1,4,4a,8a-tetrahydroquinolines 8.
- Akiba, Kin-ya,Ohtani, Akira,Yamamoto, Yohsuke
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p. 5328 - 5332
(2007/10/02)
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