A novel push-pull Diels-Alder diene: reactions of 4-alkoxy- or 4-phenylsulfenyl-5-chalcogene-substituted 1-phenylpenta-2,4-dien-1-one with electron-deficient dienophiles.
5-(phenylselenenyl)- and 5-(phenylsulfenyl)-4-ethoxy-1-phenyl-2,4-pentadien-1-ones (2) and (3) underwent [4+2] cycloaddition with N-methyl and N-phenylmaleimides and successive isomerization to give the 7-benzoyl-3a,4,5,7a-tetrahydro-1H-isoindole-1,3(2H)-diones 5, 8 and 9 in good yields. The 4-ethoxy group on the 2,4-pentadien-1-one was found to be effective to facilitate the cycloaddition with dienophiles. We also performed other [4+2] cycloadditions of 2,4-pentadien-1-ones with DMAD or naphthoquinone.
Yoshimatsu
Mitsuhiro
M
Department of Chemistry, Faculty of Education, Gifu University, Japan. yoshimae@cc.gifu-u.ac.jp
Hibino
Masaru
M
Ishida
Masaru
M
Tanabe
Genzoh
G
Muraoka
Osamu
O
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D018011:Chalcogens / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D004583:Electrons; D013237:Stereoisomerism
D000466:Alkadienes; D018011:Chalcogens