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  • 02월 19일 10시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능
대회명 대한화학회 제121회 학술발표회 및 총회
등록일 2018년 1월 23일 14시 50분 18초
접수번호 3250
발표코드 ORGN.P-313 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간 4월 19일 (목요일) 11:00~12:30
발표형식 포스터
발표분야 Organic Chemistry
저자 및 공동저자 NamRim Heo, Younghyeon Baek, Phil Ho Lee*
Department of Chemistry, Kangwon National University, Korea
제목 Regioselective Synthesis of Indolopyrazines through a Sequential Rhodium-Catalyzed Formal [3 + 3] Cycloaddition and Aromatization Reaction of Diazoindolinimines with Azirines

Indolopyrazines possessing both indole and pyrazine moieties are significant structural motifs in a number of naturally occurring products, show a wide range of biological activities, including antitumor and antiviral activities, and function as fluorescent and host materials. In this regard, the indolopyrazine motif has continuously received the attention of synthetic chemists. Thus, establishing synthetic approaches for preparing regioselective indolopyrazines from simply attainable starting materials is highly demanded. We developed a regioselective synthetic method to prepare indolopyrazines through a sequential Rh-catalyzed formal [3 + 3] cycloaddition and aromatization reaction of a wide range of diazoindolinimines with azirines. Because the previously reported synthetic methods afforded mixtures of indolopyrazines, the present method using unsymmetrical azirines has the an excellent merit from a regioselectivity standpoint. Because indolopyrazines are fluorescent, their optical properties in CH2Cl2 solution were studied. The extinction coefficients were variable from 107,298 to 585,478 M-1cm-1. The indolopyrazine affords high quantum yields and extinction coefficients, which are an attractive property for biological probes. This work was supported by the Human Resource Training Program for Regional Innovation and Creativity through the Ministry of Education and National Research Foundation of Korea(NRF-2015H1C1A1035955)

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