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제116회 대한화학회 학술발표회, 총회 및 기기전시회 안내 N-Imidazolylation of Sulfoximines from N-Cyano Sulfoximines, 1-Alkynes, and N-Sulfonyl Azides

등록일
2015년 8월 27일 15시 55분 53초
접수번호
0937
발표코드
ORGN.P-379 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 15일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
김상혁, 최원석, 이필호*
강원대학교 화학과, Korea
Sulfoximines are significant privileged scaffolds, which are extensively found in bioactive compounds, chiral auxiliaries, and ligands in asymmetric synthesis. In consequence, the development of efficient synthetic approaches for sulfoximines and their functionalizations have been continuously required. In particular, N-(hetero)aryl sulfoximines are attractive due to the fact that a multitude of their derivatives exhibited anticancer activity or proved useful as agrochemicals. Recently, a synthetic method using N-sulfonyl-1,2,3-triazoles as precursors of α-imino Rh carbenoid has been widely studied. Especially, Fokin and Lee described that Rh-catalyzed reaction of 1,2,3-triazoles with nitriles and bromocyanides afforded imidazoles and 2-bromoimidazoles, respectively. In our continuing studies related to the synthesis of nitrogen heterocyclic compounds using N-sulfonyl-1,2,3-triazoles, we envisioned that if N-cyano sulfoximines would be used as nucleophile in reacting with N-sulfonyl-1,2,3-triazoles, N-imidazolyl sulfoximines would be obtained via denitrogenative [3 + 2] cycloaddition. Herein, we demonstrate Rh-catalyzed N-imidazolylation of N-sulfonyl-1,2,3-triazoles with a variety of N-cyano sulfoximines for the synthesis of N-imidazolyl sulfoximines via elimination of molecular nitrogen. Moreover, Cu-catalyzed [3 + 2] cycloaddition followed by Rh-catalyzed N-imidazolylation from 1-alkynes, N-sulfonyl azides, and N-cyano sulfoximines is developed for the synthesis of N-imidazolyl sulfoximines in one-pot.

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