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제109회 대한화학회 학술발표회, 총회 및 기기전시회 안내 The first intramolecular Fischer indolization and its combination with aromatic Claisen rearrangement for the synthesis of tricyclic benzo[cd]indole

2012년 2월 16일 17시 47분 44초
ORGN.P-919 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
4월 25일 (수요일) 18:00~21:00
저자 및
박준, 박인걸, 조천규
한양대학교 화학과, Korea

We have previously demonstrated that aryl hydrazides are effective surrogates of aryl hydrazines, undergoing the Fischer indolization reaction to afford the corresponding indoles, when treated with enolizable aldehydes and ketones in the presence of an acid. Unlike aryl hydrazines, the aryl hydrazides are readily accessed from aryl halides via the Pd(0) or Cu(I)-catalyed coupling reaction with N-Boc hydrazine. We have also reported that N-Cbz-aryl hydrazide can proceed in a Fischer indolization reaction to give N-cbz-indole without the elimination of N-Cbz group. Prompted by our recent interest on the synthesis of ergot alkaloids, we set out to study the intramolecular Fischer indolization reaction of the aryl hydrazide that are linked to carbonyl functions by various tether groups as a new synthetic means to the construction of tricyclic indole system. We found that aryl hydrazide with carbonyl function tethered at the C(4) postion of the aromatic ring undergoes intramolecular Fischer indolization to afford novel indolophanes. In addition, strategic insertion of a double bond in the tether allowed for an aromatic Claisen rearrangement to proceed in a tandem fashion, providing tricyclic benzo[cd]indole system.