Dong Chun-Ping, Kodama Shintaro, Nomoto Akihiro, Ueshima Michio, Ogawa Akiya
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.
ACS Omega. 2019 May 23;4(5):9029-9040. doi: 10.1021/acsomega.9b00999. eCollection 2019 May 31.
4,6-Dihydroxysalicylic acid was activated under air to catalyze the one-pot oxidative condensation reaction of benzylamines with acetophenones in the presence of BF·EtO, affording 2,4,6-trisubstituted pyridines in yields of 59-91%. During this metal-free oxidative condensation reaction, the benzylamines not only provided the aryl moiety at the 4-position of the pyridines but also acted as the nitrogen donor. This method can be applied to the metal-free synthesis of G-quadruplex binding ligands by the sequential addition of 4-chlorobutyryl chloride and pyrrolidine to the reaction system of the 2,4,6-trisubstituted pyridine synthesis.
4,6-二羟基水杨酸在空气中被活化，以催化苄胺与苯乙酮在BF·EtO存在下的一锅氧化缩合反应，得到产率为59-91%的2,4,6-三取代吡啶。在这个无金属氧化缩合反应中，苄胺不仅在吡啶的4-位提供芳基部分，还作为氮供体。通过将4-氯丁酰氯和吡咯烷依次加入到2,4,6-三取代吡啶合成的反应体系中，该方法可应用于无金属合成G-四链体结合配体。
