新型荧光功能单体2,4-二甲基-7-丙烯酰胺基-1,8-萘啶的合成及其光谱特性

Synthesis and Spectral Characterization of a Novel Fluorescent Functional Monomer 2,4-Dimethyl-7-Acrylamine-1,8-Naphthyridine

设计合成了可与DNA碱基通过氢键选择性结合的新型荧光功能单体2，4-二甲基-7-丙烯酰胺基-1，8-萘啶（DMAAN）。其反应原理是，2，6-二胺基吡啶与乙酰丙酮在磷酸介质中反应生成中间产物2，4-二甲基-7-胺基-1，8-萘啶（DMAN）。DMAN与丙烯酰氯在三乙胺存在下，于氯仿溶剂中反应即可得到熔点为239～241℃的产物。采用^1H核磁共振波谱、质谱、紫外-可见光谱对中间产物DMAN和目标化合物DMAAN进行了光谱表征，并进一步研究了其荧光光谱特性。

A new fluorescent functional monomer DMAAN has been designed and synthesized for the first time. The monomer was expected to bind with cytosine via complementary hydrogen bonding under certain experimental conditions. The synthetic procedure of DMAAN is as follows. A suspension of 2,6-diaminopyridine in phosphoric acid was added to acetylacetone. The mixture was warmed for thirty minutes on a steam-bath. Then 2,4-dimethyl-7-amino-1,8-naphthyridine（DMAN, mp 216-218 ℃ ） was obtained. DMAAN was prepared by the reaction of DMAN with acryloyl chloride in chloroform and triethylether mixed solvent. Acryloyl chloride in anhydrous chloroform was added dropwise over 30 minutes with constant stirring at 4℃. The melting point of the final product was 239-241℃. Mass spectrometry and proton NMR were used to confirm the chemical structure of DMAN and DMAAN. The products were also characterized by UV and fluorescence spectrometry.