Synthesis of Novel Azopyrazolo-[1,5-A]Pyrimidine Derivatives

合成新穎之偶氮吡唑[1,5-a]嘧口定衍生物

何玉文(Yuh-Wen Ho)

《桃園創新學報》 32期 (2012/12) Pp. 1-14

https://doi.org/10.6989/JTI.201212.0001

摘要

具取代基之對胺苯磺醯胺基（aminosulfanilamide）衍生物經重氮化反應後與氰基乙酸乙酯化合物進行偶合反應得到苯腙衍生物2a-d。接著苯腙衍生物2a-d在乙醇溶劑下與水合月井進行環化反應得3－胺基偶氮口比唑衍生物3a-d。將合成之3－胺基偶氮口比唑衍生物3a-d與雙硫化甲基亞甲基丙二月青4在DMF及三乙醇胺存下進行環化縮合反應，得到新穎之取代基偶氮口比唑[1,5-a]嘧口定衍生物6a-d。將合成之6a, d再與對－甲氧基苯胺反應，得到苯胺基衍生物8a, b。所合成之新化合物經紅外線光譜（IR）、核磁共振（1H-NMR）、質譜儀（MS）及元素分析（EA）確定其結構。

關鍵字

偶氮口比 ； 唑[1,5-a]嘧 ； 口定衍生物 ； 環化縮合反應 ； 對胺苯磺醯胺基衍生物 ； 重氮化反應

並列摘要

Hydrazones 2a-d were prepared from diazotiazation of sulfanilamide or its derivatives followed by coupling with ethyl cyanoacetate. 3-Aminopyrazoles 3a-d was obtained by refluxing of 2a-d with hydrazine hydrate in ethanol. [Bis(methylthio)- methylene]malononitrile (4) was reacted with aminopyrazoles 3a-d in refluxing DMF containing triethylamine to yield the corresponding azopyrazolo[1,5-a]pyrimidines 6a-d. The anilino derivatives 8a, b were also obtained by fusion of compounds 6a, d with p-anisidine. The structure of the new compounds was substantiated from their IR, 1H-NMR, Mass spectra and elemental analysis.

並列關鍵字

Azopyrazolo [1,5-a] pyrimidine derivatives ； Cyclocondensation ； Aminosulfanilamide ； Diazotiazation