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

K Akiba, A Ohtani, Y Yamamoto

Index: Akiba, Kin-ya; Ohtani, Akira; Yamamoto, Yohsuke Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5328 - 5332

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Citation Number: 21

Abstract

(Danishefsky's dieneg) at 100" C for 7 h in toluene. However, when 4g was heated with 2 equiv of 3, 4-dichlorothiophene 1, l-dioxide (7)'O in refluxng toluene for 12 h, a rather complex mixture was obtaizled from which the expected adduct 8g was isolated in 15% yield. Other products included recovered 4g (4%), the dimer of 7, and methyl nicotinate (1, 36%), probably formed by the decomposition of 4g. The fact that 8g was obtained ...