Novel Thieno[32-b]pyridine-54H-one Derivatives method for preparing therefor and use of the same

The present invention relates to a novel derivative compound of thieno[3,2-b]pyridine-5(4H)-one, a method of preparing the same, and uses of the same. According to the present invention, the novel derivative compound of thieno[3,2-b]pyridine-5(4H)-one is synthesized via aza-[3+3] cycloaddition using BOP, and in particular, 4-arylthiophen-3-amine with aryl groups, such as 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, and 4-F3COC6H4, introduced therein, is synthesized from methyl 3-aminothiophene carbosylate through synthesis processes involving bromination, hydrolysis, decarboxylation, and Suzuki coupling reactions, and 4-arylthiophen-3-amine and mono-methyl fumarate are synthesized via aza-[3+3] cycloaddition and conjugation using BOP. According to the present invention, the novel derivative compound of thieno[3,2-b]pyridine-5(4H)-one has fluorescent characteristics with a wide range of emission wavelengths, and thus may be beneficially used in various industries such as research in physics, chemistry, and biomedicine. 본 발명은 신규한 티에노[3,2-b] 피리딘-5(4H)-온 유도체 화합물, 이의 제조방법 및 이의 용도에 관한 것이다. 본 발명에 따른 신규한 티에노[3,2-b] 피리딘-5(4H)-온 유도체 화합물은 BOP를 이용한 aza-[3+3]고리화 첨가 반응을 통해 합성한 것으로, methyl 3-aminothiophene carbosylate의 브로민화 반응, 가수분해 반응, 탈카복실화 반응, Suzuki 커플링 반응에 의한 합성 과정을 통해 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, 4-F3COC6H4 등의 아릴기를 도입한 4-arylthiophen-3-amine을 합성하였고, 4-arylthiophen-3-amine과 mono-methyl fumarate를 BOP를 이용한 formal aza-[3+3] 고리화 첨가 반응과 콘주게이션을 통해 합성된 것으로, 본 발명에 따른 신규한 티에노[3,2-b] 피리딘-5(4H)-온 유도체 화합물들은 광범위한 영역의 방출파장을 갖는 형광특성을 가지므로, 물리, 화학, 바이오의료 연구 등 다양한 산업분야에서 유용하게 사용할 수 있다.