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학술발표회초록보기

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

제116회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Diazotization followed by Intramolecular Cyclization from Pyridinylarylacetates in One-Pot : Synthesis of Pyridoisoindoles

등록일
2015년 8월 27일 15시 55분 51초
접수번호
0934
발표코드
ORGN.P-376 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 15일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
김철의, 신서현, 이필호*
강원대학교 화학과, Korea
Pyridoisoindoles are key priviledged scaffolds in nitrogen-containing heterocyclic compounds, which are widely found in pharmaceuticals, natural products, fluorescent materials, and dyes. Accordingly, development of synthetic methods for preparing pyridoisoindoles having a variety of functional groups represents a considerable task and a significant challenge. Although these functionalizations of pyridoisoindole derivatives have been reported, a limited number of synthetic methods have been described. Thus, a robust synthesis of pyridoisoindole derivatives has been continuously needed. Especially, it is very significant to introduce a wide range of functional groups onto pyridoisoindoles and to prepare 6-ethoxycarbonyl pyridoisoindoles. Moreover, preparation of pyridoisoindole derivatives having other nitrogen heterocycles besides pyridine provides a synthetic challenge. Herein, we have developed a robust synthetic method for a wide range of pyridoisoindoles from pyridinylarylacetates in one-pot through diazotization using TsN3 and DBU followed by intramolecular cyclization via elimination of nitrogen molecule under Cu(OTf)2-catalyzed conditions. Also, the intramolecular cyclization took place efficiently with diazo substrates to furnish pyridoisoindoles in good to excellent yields under metal-free conditions or Cu(OTf)2-catalyzed conditions at room temperature.

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