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제120회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthesis of 2-Functionalized Tropones through Sequential Functionalization of O-H and C(sp2)-O Bonds of Tropolones

등록일
2017년 8월 3일 16시 09분 52초
접수번호
0207
발표코드
ORGN.P-255 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 20일 (금요일) 13:00~14:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
Boram Seo, Minhyeon Byeon, Phil Ho Lee*
Department of Chemistry, Kangwon National University, Korea

Tropones make up a significant class of seven-membered non-benzenoid aromatic compounds that can be subjected to higher order cycloaddition reactions to provide a large number of biologically active compounds and natural products. Aminotroponimines derived from tropolone having a 2-hydroxy group are also a typical group of ligands. In this regard, introduction of new functional groups onto tropone and transformation of previously present functional groups in the troponoid family are desirable. Although there are several methodologies for the preparation of functionalized tropones in the literature, the development of new and convenient methods to prepare them is imperative. For this reason, we have developed the Rh-catalyzed reaction of tropolones with N-tosyl-1,2,3-triazoles for the synthesis of the 2-functionalized aminotropones via tandem Rh-catalyzed O−H insertion, intramolecular 1,8-addition, and rearrangement in one pot. Sequential Cu-catalyzed [3 + 2] cycloaddition, Rh-catalyzed O−H insertion, intramolecular 1,8-addition, and rearrangement starting from 1-alkynes, N-sulfonyl azides, and tropolones is also demonstrated for the synthesis of the 2-functionalized aminotropones in one pot. These results suggest that sequential functionalization of O−H and C(sp2)−O bonds smoothly take place in C(sp2)−O−H bonds at the 2-position of tropolone.


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