Novel synthesis of cinnolines and 1-aminoindolines via Cu-catalyzed intramolecular N-arylation of hydrazines and hydrazones prepared from 3-haloaryl-3-hydroxy-2-diazopropanoates.
Novel synthesis of cinnolines and 1-aminoindolines via Cu-catalyzed intramolecular N-arylation of hydrazines and hydrazones prepared from 3-haloaryl-3-hydroxy-2-diazopropanoates.
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DOI：
10.1021/jo8010864
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发表时间：
2008-07
期刊：
影响因子：
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通讯作者：
Kazuya Hasegawa;N. Kimura;S. Arai;A. Nishida
中科院分区：
文献类型：
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作者：
Kazuya Hasegawa;N. Kimura;S. Arai;A. Nishida
通过重氮官能团的使用，建立了一种新的和容易获得的噌啉，二氢噌啉和1-氨基吲哚啉。利用相转移催化一锅法制备的3-卤代芳基-3-羟基-2-重氮丙酸酯衍生物作为环化前体的肼和腙，通过铜催化的N-芳基化成功转化为相应的氮杂环。此外，紫外光谱分析证明，4-氧代-3-羧酸酯主要不是以4-羟基噌啉（烯醇形式）存在，而是以噌啉酮（酮形式）存在。
A new and facile access to cinnolines, dihydrocinnolines, and 1-aminoindolines was established by use of diazo functionalities. The hydrazines and hydrazones as cyclization precursors derived from 3-haloaryl-3-hydroxy-2-diazopropanoates, which are prepared by one-pot procedure utilizing phase-transfer catalysis, are successfully converted to the corresponding nitrogen heterocycle by Cu-catalyzed N-arylation. Furthermore, analysis of UV spectra proved that 4-oxo-3-carboxylates predominantly exist not as 4-hydroxycinnoline (enol form) but as cinnolone (keto form).