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Synthesis of Indolizine Derivatives and Their Reactions

Chikatoshi Maseda, MASAKATSU SONE, Yoshinori Tominaga, REIKO NATSUKI, Yoshiro Matsuda, Goro Kobayashi

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Abstract

Indo1izine derivatives (II and V) were synthesized by the reaction of α-bismethyl-thiomethylene-2-pyridineacetonitrile (I) and dimethyl N-(2-pyridyl)-dithiocarbimidate (III) with α-haloketone compound, ethyl γ-bromocrotonate. Reaction of I with nitromethane afforded 1-cyano-2-methylthio-3--nitrosoindolizine (VIII). Dimethyl 1-carbamoyl-2-methyl thiocycl [3, 2, 2] azine-3, 4-dicarboxylate (XI) was obtained from the indolizine derivative (IX) and dimethyl acetylenedicarboxylate.

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Indo1izine derivatives (II and V) were synthesized by the reaction of α-bismethyl-thiomethylene-2-pyridineacetonitrile (I) and dimethyl N-(2-pyridyl)-dithiocarbimidate (III) with α-haloketone compound, ethyl γ-bromocrotonate. Reaction of I with nitromethane afforded 1-cyano-2-methylthio-3--nitrosoindolizine (VIII). Dimethyl 1-carbamoyl-2-methyl thiocycl [3, 2, 2] azine-3, 4-dicarboxylate (XI) was obtained from the indolizine derivative (IX) and dimethyl acetylenedicarboxylate.

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Available abstract

Indo1izine derivatives (II and V) were synthesized by the reaction of α-bismethyl-thiomethylene-2-pyridineacetonitrile (I) and dimethyl N-(2-pyridyl)-dithiocarbimidate (III) with α-haloketone compound, ethyl γ-bromocrotonate. Reaction of I with nitromethane afforded 1-cyano-2-methylthio-3--nitrosoindolizine (VIII). Dimethyl 1-carbamoyl-2-methyl thiocycl [3, 2, 2] azine-3, 4-dicarboxylate (XI) was obtained from the indolizine derivative (IX) and dimethyl acetylenedicarboxylate.

Key concepts: Indolizine, Dimethyl acetylenedicarboxylate, Nitromethane, Azine, Chemistry, Medicinal chemistry, Derivative (finance), Organic chemistry

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