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题名: Multiple reactivities of dithranol towards 1-alkynyl Fischer carbene complexes (CO)(5)M=C(OEt)C CPh (M = Cr, W) - Efficient chemical synthesis of aromatic polyketides
作者: Luo, Ning1;  Yu, Zhengkun1, 2
关键词: Fischer carbene ;  Dithranol ;  Multiple reactivity ;  Polyketides ;  Polycarbene
刊名: JOURNAL OF ORGANOMETALLIC CHEMISTRY
发表日期: 2009-09-01
DOI: 10.1016/j.jorganchem.2009.05.029
卷: 694, 期:19, 页:3058-3067
收录类别: SCI ;  IC
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Inorganic & Nuclear ;  Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: Reactions of anti-psoriasis drug dithranol with 1-alkynyl Fischer carbene complexes (CO)(5)M =C(OEt)C CPh (M = Cr, W) were investigated under controlled conditions in which triethylamine-promoted C-addition, O-addition, electrophilic aromatic substitution, and cyclization consecutively occurred at up to five positions of dithranol. A remarkable solvent effect led to selective formation of polyphenolic organic and organometallic mono- and triscarbene complexes which were efficiently demetalated to the potentially bioactive aromatic polyketides with pyridine-N-oxide. All the organic and organometallic products were characterized by methods including X-ray single crystal structural determinations. These results have revealed the novel multiple reactivities of dithranol which might be associated to its clinical side effect, providing a new synthetic methodology to functionalize dithranol for medical purposes, and chemically synthesize aromatic polyketides. (C) 2009 Elsevier B. V. All rights reserved.
关键词[WOS]: H INSERTION ;  PATHWAY ;  CHROMIUM ;  DEMETALATION ;  ANTHRACENE
语种: 英语
WOS记录号: WOS:000268799500003
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/141623
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

Recommended Citation:
Luo, Ning,Yu, Zhengkun. Multiple reactivities of dithranol towards 1-alkynyl Fischer carbene complexes (CO)(5)M=C(OEt)C CPh (M = Cr, W) - Efficient chemical synthesis of aromatic polyketides[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY,2009,694(19):3058-3067.
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