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제123회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthesis of Indole Derivatives Using Diazoindolinimines

등록일
2019년 2월 14일 14시 24분 32초
접수번호
4426
발표코드
ORGN2-1 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
금 09시 : 00분
발표형식
심포지엄
발표분야
Organic Chemistry - Current Trends in Organic Chemistry II: Synthetic Methodology and Catalysis
저자 및
공동저자
Phil Ho Lee
Department of Chemistry, Kangwon National University, Korea
Rh-catalyzed cyclization reaction of sulfoximines with 3-diazoindolinimines is described. This protocol provided a wide range of indolobenzothiazines together with the release of molecular nitrogen and p-toluenesulfonamide. The present method involved the N−H/C−H activation of S-aryl sulfoximines and has the advantages of a broad substrate scope. A regioselective synthetic method for the preparation of pyrazinoindoles was demonstrated 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 pyrazinoindoles, the present method using unsymmetrical azirines has a strong advantage from a regioselectivity viewpoint. Rh-catalyzed formal aza-[4 + 3] cycloaddition reaction of 3-diazoindolinimines with 1,3-dienes was demonstrated for the synthesis of azepinoindoles in one-pot. First, Rh-catalyzed [2 + 1] cycloaddition reaction smoothly took place to produce iminyl vinyl cyclopropane intermediate at room temperature in chlorobenzene, which was thermally converted to azepinoindoles via aza-Cope rearrangement.

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