title: Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines.
abstract: 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.
authors.affiliation: Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500670, India. plikhar@iict.res.in
authors.forename: Pravin R
authors.initials: PR
authors.lastname: Likhar
authors.forename: Madavu Salian
authors.initials: MS
authors.lastname: Subhas
authors.forename: Sarabindu
authors.initials: S
authors.lastname: Roy
authors.forename: Mannepalli Lakshmi
authors.initials: ML
authors.lastname: Kantam
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.forename: Ratanesh Kumar
authors.initials: RK
authors.lastname: Seth
authors.forename: Sukla
authors.initials: S
authors.lastname: Biswas
mesh_terms: 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
chemical_list: D000588:Amines; D000962:Antimalarials; D007097:Imines; D011804:Quinolines; D002244:Carbon