Synthesis of cycl [3.2. 2] azine and benzo [g] cycl [3.2. 2] azine derivatives by use of the [2+ 8] cycloaddition reaction of indolizines and dimethyl …

Y Tominaga, Y Shiroshita, T Kurokawa…

Index: Tominaga, Yoshinori; Shiroshita, Yoshihide; Kurokawa, Tomohiko; Gotou, Hiromi; Matsuda, Yoshiro; Hosomi, Akira Journal of Heterocyclic Chemistry, 1989 , vol. 26, p. 477 - 487

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Citation Number: 19

Abstract

Abstract The reaction of 1-ethoxycarbonylmethylpyridinium bromides 5a-k with nitro ketene dithioacetal, 1, 1-bis-(methylthio)-2-nitroethylene (2), in the presence of triethylamine in ethanol gave the desired ethyl 2-methyl-thioindolizine-3-carboxylates 3a-k in good yields, along with ethyl 2-methylthio-1-nitroindolizine-3-carboxyl-ates 4a-d. Deesterification of 3 using sodium hydroxide in methanol followed by treatment with polyphosphoric acid gave ...