119th General Meeting of the KCS

Type Poster Presentation
Area 의약화학
Room No. 포스터발표장
Time 4월 20일 (목요일) 11:00~12:30
Code MEDI.P-427
Subject Synthesis of Dipyrrolopyrazine (DPP) Derivatives via Metal Free and Metal Catalyzed Regioselective Amination and Investigation of Their Optical and Thermal Properties
Authors Puttavva meti, 이은실1, 공영대*
동국대학교 화학과, Korea
1동국대학교 의약화학연구실, Korea
Abstract Pyrazine is an important molecular scaffold employed in organic optoelectronic materials. Here we report efficient methods for the synthesis of dipyrrolopyrazine, and pyrrolothieno-pyrazine derivatives that involve regio-selective amination reactions of dihalo-pyrrolopyrazines. The developed protocol readily affords either 2-amino- or 3-amino-pyrrolopyrazines from the corresponding 2-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazines. When the amination reactions are carried under metal free under microwave irradiation, 3-amino-pyrrolopyrazines are obtained exclusively. In contrast, Buchwald cross coupling of the 2-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazines affords only 2-amino-pyrrolopyrazine. The pyrrolopyrazine scaffolds were converted to the respective 1,7- and 1,5-dihydrodipyrrolo[2,3-b]pyrazines derivatives using Sonogashira reactions. A comprehensive study of the optical properties, thermal properties, and molecular packing of the synthesized compounds was carried out. The results indicate that the 1,7-derivatives may be promising organic materials for optoelectronic applications.
E-mail pmeti25@gmail.com