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题名: Tautomerism-dependent ring construction of N-heterocyclic compounds from the reactions of 1-alkynyl Fischer carbene complexes and substituted pyrazolinones
作者: Zheng, Zhaoyan;  Yu, Zhengkun;  Luo, Ning;  Han, Xiuwen
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2006-12-22
DOI: 10.1021/jo061725+
卷: 71, 期:26, 页:9695-9700
收录类别: SCI ;  IC ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: Four types of N-heterocyclic ring systems were successfully constructed from the reactions of 1-alkynyl Fischer carbene complexes (OC)(5)M=C(OEt)C CPh (1) (M = Cr, W) and substituted pyrazolinones (2). Reactions of 1 with 3-methyl-2-pyrazolin-5-one (2a), 3-n-propyl-2-pyrazolin-5-one (2b), 3,4-dimethyl-2-pyrazolin-5-one (2c), 3,4-trimethylene-2-pyrazolin-5-one (2d), or 3,4-tetramethylene-2-pyrazolin-5-one (2e) generated three kinds of Fischer aminocarbene complexes (3-5), and reactions of 1 with phenyl-substituted pyrazolinones, i.e., 3-phenyl-2-pyrazolin-5-one (2f) and its tautomer 3-phenyl-3-pyrazolin-5-one (2g), gave Fischer alkoxycarbene complexes ( 6) as the major products and aminocarbene complexes of types 3-5 as the minor products. Multiple tautomerism of pyrazolinones is attributed to the versatile formation of N-heterocyclic Fischer carbene complexes. Oxidative demetalation of complexes 3-6 with pyridine N-oxide or m-chloroperoxybenzoic acid efficiently afforded organic carbonyl products, and thus, strongly fluorescent syn-mixed-bimanes were prepared. The present findings constitute an alternative new method to synthesize mixed bimanes and other novel N-heterocyclic compounds.
关键词[WOS]: TRANSITION-METAL COMPLEXES ;  ORGANIC SYNTHESES ;  ANTI-1,5-DIAZABICYCLO<3.3.0>OCTADIENEDIONES 9,10-DIOXABIMANES ;  ALKYNYLCARBENE COMPLEXES ;  CYCLOADDITION REACTIONS ;  CHEMICAL MULTITALENTS ;  ASYMMETRIC-SYNTHESIS ;  MICHAEL ADDITION ;  CHROMIUM ;  BIMANES
语种: 英语
WOS记录号: WOS:000242845500017
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140246
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, State Key Lab Catalysis, 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:
Zheng, Zhaoyan,Yu, Zhengkun,Luo, Ning,et al. Tautomerism-dependent ring construction of N-heterocyclic compounds from the reactions of 1-alkynyl Fischer carbene complexes and substituted pyrazolinones[J]. JOURNAL OF ORGANIC CHEMISTRY,2006,71(26):9695-9700.
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