Likhar Pravin R, Subhas Madavu Salian, Roy Sarabindu, Kantam Mannepalli Lakshmi, Sridhar Balasubramanian, Seth Ratanesh Kumar, Biswas Sukla
Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500670, India.
Org Biomol Chem. 2009 Jan 7;7(1):85-93. doi: 10.1039/b815398a. Epub 2008 Nov 10.
A series of highly substituted 2-perfluoroalkyl-3-iodoquinolines are prepared by two different methods in good to excellent yields under mild reaction conditions. The first method involves iodocyclization of perfluoroalkyl propargyl imines with I(2)-CAN. The second method involves iodocyclization of perfluoroalkyl propargyl amines using I(2) and ICl. The perfluoroalkyl propargyl amines are prepared in excellent yields via Sonogashira coupling of easily accessible imidoyl iodides with alkynes followed by reduction with NaBH(3)CN. The scope of this methodology is extended by using the resulting 2-perfluoroalkyl-3-iodo quinolines in Suzuki, annulation, dehalogenation and carboxylation reactions. Antimalarial activity of the 2-perfluoroalkyl-3-iodoquinolines is discussed.
一系列高度取代的2-全氟烷基-3-碘喹啉通过两种不同方法在温和反应条件下以良好至优异的产率制备。第一种方法涉及全氟烷基炔丙基亚胺与I(2)-CAN的碘环化反应。第二种方法涉及使用I(2)和ICl对全氟烷基炔丙基胺进行碘环化反应。全氟烷基炔丙基胺通过易于获得的亚氨基碘化物与炔烃的Sonogashira偶联反应，然后用NaBH(3)CN还原，以优异的产率制备。通过将所得的2-全氟烷基-3-碘喹啉用于铃木反应、环化反应、脱卤反应和羧化反应，扩展了该方法的适用范围。讨论了2-全氟烷基-3-碘喹啉的抗疟活性。
