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  • 09월 08일 17시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제116회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthesis of terphenyl type unsymmetrical phenylene bis-(1H-pyrrole) derivatives from nitroanilines and 1,4-dicarbonyls

등록일
2015년 8월 27일 16시 52분 27초
접수번호
1063
발표코드
ORGN.P-396 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 15일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
배설희, 김병효*, 이병민1
광운대학교 화학과, Korea
1한국화학연구원 게면화학공정연구센터, Korea
Pyrroles are useful in many research areas because of its broad applications as conducting polymers, pharmaceutical agents, and building blocks in natural products such as vitamin B12 or hemoglobin. Basic concept of the Paal-Knorr condensation which consists the cyclocondensation of primary amine with 1,4-carconyl compound remains as the most attractive and the easiest method for the synthesis of pyrroles. Also indium metal is widely used for organic synthesis because it has an advantage of low toxicity and good stability in the air or oxygen at room temperature. Herein we report the development of new synthetic strategy to two unsymmetrically substituted phenylene bis-pyrroles using Paal-Knorr condensation reaction followed by reduction-triggered intermolecular heterocyclization starting from nitroanilines with proper 1,4-dicarbonyls. Firstly, Paal-Knorr condensation reaction of nitroanilines with a first 1,4-diketone in the presence of p-TsOH was done and it produced nitrophenyl-1H-pyrroles in good yield (50-99%). Then, obtained nitrophenyl-1H-pyrroles were reacted with the second 1,4-diketones that are different from the first 1,4-diketones of Paal-Knorr reaction in the presence of indium/acetic acid, which resulted in two distinctive bis-pyrrole-containing arenes in reasonable yield (40-92%).

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