121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-393
Subject Indium-mediated reductive reactions of highly electron deficient nitroanilines towards two distinctive bis-pyrrole-containing arenes
Authors EUNGYUNG KIM, Byung Min Lee1, BYEONG HYO KIM*
Department of Chemistry, Kwangwoon University, Korea
1Center for Interface Materials and Chemical Engine, Korea Research Institute of Chemical Technology, Korea
Abstract Pyrrole moiety is an important heterocyclic structure found in natural products and bioactive molecules including anti-inflammatants and immunosuppressants. In particular, polypyrroles (PPys) have proven their great potential in the fabrication of microelectronic and optoelectronic devices, including field effect transistors, organic light-emitting diodes (OLED), because of their good thermal and oxidative stability, flexibility and electrical conductivity. Most of the synthetic approach using highly electron-deficient anilines towards pyrroles for N-hetero cyclization encountered difficulties because of their poor reactivity. Consequently, their biological or electronic usefulness is barely investigated. Therefore, synthetic transformation of highly electron deficient nitroanilines to two distinctive bis-pyrrole-containing arenes was investigated in this study. Indium-mediated reductive cyclization of highly electron deficient 2,6-disubstituted nitroanilines with 1,4-diketone to 2,6-disubstituted 4-(1H-pyrrol-1-yl)aniline followed by a ring annulation via Paal-Knorr reaction with another 1,4-diketone resulted in bis-pyrrole-containing electron-deficient arenes, in reasonable yield.
E-mail ejkj76@naver.com