Synthesis ( IF 2.2 ) Pub Date : 2018-01-24 , DOI: 10.1055/s-0036-1591884 Dong-Liang Mo , Xiao-Hua Li , Ai-Hui Ye , Cui Liang
‡ X.-H. Li and A.-H. Ye contributed equally to this work
Abstract
An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y1 lead compound analogue could be prepared in good yield over two steps.
An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y1 lead compound analogue could be prepared in good yield over two steps.
中文翻译:
2-吡啶酮对二芳基碘鎓盐的选择性O-芳基化的取代作用:在无过渡金属的条件下合成2-芳氧基吡啶
‡ X.-H. 李和A.-H. 叶对此工作做出了同样的贡献
抽象的
通过2-吡啶酮与二芳基碘鎓盐的选择性O-芳基化反应,已经开发了一种有效的无过渡金属合成2-芳氧基吡啶衍生物的策略。该反应与2-吡啶酮和二芳基碘鎓盐的一系列官能团相容,例如卤化物,硝基,氰基和酯基。由于空间位阻,在2-吡啶酮的C 6位上的取代基有利于O-芳基化产物。该反应易于以克为单位进行,并且6-氯-2-吡啶酮是通过脱卤作用获得各种未取代的2-芳氧基吡啶的良好前体。可以通过两个步骤以高收率制备P2Y 1铅化合物类似物。
通过2-吡啶酮与二芳基碘鎓盐的选择性O-芳基化反应,已经开发了一种有效的无过渡金属合成2-芳氧基吡啶衍生物的策略。该反应与2-吡啶酮和二芳基碘鎓盐的一系列官能团相容,例如卤化物,硝基,氰基和酯基。由于空间位阻,在2-吡啶酮的C 6位上的取代基有利于O-芳基化产物。该反应易于以克为单位进行,并且6-氯-2-吡啶酮是通过脱卤作用获得各种未取代的2-芳氧基吡啶的良好前体。可以通过两个步骤以高收率制备P2Y 1铅化合物类似物。