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学科主题: 天然产物有机化学
题名: A one-pot assembly of 4-allyl-3-pyridinecarboxaldehyde. A new synthesis of 1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine, an annulated nicotine analogue
其他题名: 一种环状尼古丁类似物的新合成方法
作者: Luo SJ(罗盛军) ; Fang F(方芳) ; Zhao MY(赵明月) ; Zhai HB(翟宏斌)
通讯作者: 翟宏斌
刊名: Tetrahedron
发表日期: 2004
卷: 60, 期:25, 页:5353-5355
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所现代有机合成实验室; 河南郑州烟草研究所
英文摘要: This paper describes a two-step synthesis of 1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine, a conformationally constrained nicotine analogue. The target molecule was effectively assembled by an intramolecular azomethine ylide-alkene [3+2] cycloaddition. The cyclization precursor, 4-allyl-3-pyridinecarboxaldehyde, was formed efficaciously in a single step from 3-pyridinecarboxaldehyde via sequential in situ protection, ortho lithiation, cuprate formation, allylation, and deprotection. The cuprate formation plays a vital role in minimizing/eliminating the extent of multiple alkylation. (C) 2004 Elsevier Ltd. All rights reserved.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000221919500008
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/25575
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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Recommended Citation:
Luo SJ,Fang F,Zhao MY,et al. A one-pot assembly of 4-allyl-3-pyridinecarboxaldehyde. A new synthesis of 1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine, an annulated nicotine analogue[J]. Tetrahedron,2004,60(25):5353-5355.
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