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■ Synthesis of Bis(7-dimethylamino-1-indolizinyl)methane Derivatives and Their Oxidation: As an Oxidative Chromogenic Reagent in Clinical Analysis

Yoshinori Tominaga,* Sachiko Itonaga, Tetsuya Kouno, and Yasuhiro Shigemitsu

*Center of Instrumental Analysis, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Acid-catalyzed condensation of 7-dimethylaminoindolizines with aldehydes led to substituted bis(7-dimethylaminoindolizin-1-yl)methanes (3a-i) which were easily converted into substituted bis(7-dimethylaminoindolizin-1-yl)methyl cations (4a-i) by oxidation with DDQ. These triaryl cation dyes were converted to the new heterocyclic ring system, 12-dimethylamino-6,8-bis(ethoxycarbonyl)-2H-thiopyrano[3,2-a:5,6-a’]diindolizine-2-N,N-dimethylimi-nium perchlorates (5a, b), under reflux conditions in ethanol.