Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines.
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.
Likhar
Pravin R
PR
Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500670, India. plikhar@iict.res.in
Subhas
Madavu Salian
MS
Roy
Sarabindu
S
Kantam
Mannepalli Lakshmi
ML
Sridhar
Balasubramanian
B
Seth
Ratanesh Kumar
RK
Biswas
Sukla
S
D000588:Amines / Q000737:chemistry*; D000962:Antimalarials / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002855:Chromatography, Thin Layer / Q000379:methods; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013696:Temperature; D013997:Time Factors
D000588:Amines; D000962:Antimalarials; D007097:Imines; D011804:Quinolines; D002244:Carbon