Quinoxalines XV. Convenient Synthesis and Structural Study of Pyrazolo[1,5-a]quinoxalines

被引：10

作者：

Sarodnick, Gerhard ^{[1
]}

Linker, Torsten ^{[1
]}

Heydenreich, Matthias ^{[1
]}

Koch, Andreas ^{[1
]}

Starke, Ines ^{[1
]}

Fuerstenberg, Sylvia ^{[1
]}

Kleinpeter, Erich ^{[1
]}

机构：

[1] Univ Potsdam, Dept Chem, D-14476 Potsdam, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期

关键词：

PHOTODECOMPOSITION; REARRANGEMENTS;

D O I：

10.1021/jo802398g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of aryloxymethylquinoxaline oximes, hitherto unknown and synthesized from the corresponding aldehydes, afforded in only one step pyrazolo[1,5-a]quinoxalines in the presence of acetic anhydride at high temperatures. A formal [3,5]-sigmatropic rearrangement was proposed as the mechanistic rationale for this unprecedented transformation. Saponification with potassium hydroxide furnished the free phenol derivatives which were studied by NMR spectroscopy and accompanying theoretical DFT calculations, establishing, intramolecular hydrogen bonding and the spatial magnetic properties. Additionally, mass spectrometric fragmentation was investigated by B/E-linked scans and collision-induced dissociation experiments. The fragmentation pattern devoted a new gas phase rearrangement process, which proved to be unique and characteristic for pyrazolo[1,5-a]quinoxalines.

引用

页码：1282 / 1287

页数：6

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