title: Pyrano[4,3-b]quinolines library generation via iodocyclization and palladium-catalyzed coupling reactions.
abstract: Synthesis of a 80-member library of novel pyrano[4,3-b]quinolines in solution-phase is reported. The key intermediate, 4-iodopyrano[4,3-b]quinolines were synthesized by the electrophilic iodocyclization of corresponding ortho-alkynyl aldehydes in good to excellent yields under mild reaction conditions. Subsequently a diverse set of libraries was generated by employing palladium-catalyzed Suzuki-Miyaura, Heck, and Sonogashira coupling reactions on 4-iodopyrano[4,3-b]quinolines. In this way, a series of structurally different and biologically interesting molecules were obtained. Some of the selected compounds were screened against 3D7 strains of Plasmodium falciparum for antimalarial activity. Suzuki coupling products 6{3} and 6{21} and Heck coupling product 8{12} exhibit promising antimalarial activity.
authors.affiliation: Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, India.
authors.forename: Trapti
authors.initials: T
authors.lastname: Aggarwal
authors.forename: Maryam
authors.initials: M
authors.lastname: Imam
authors.forename: Naveen K
authors.initials: NK
authors.lastname: Kaushik
authors.forename: Virander S
authors.initials: VS
authors.lastname: Chauhan
authors.forename: Akhilesh K
authors.initials: AK
authors.lastname: Verma
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D011714:Pyrans; D011804:Quinolines; D054852:Small Molecule Libraries; D010165:Palladium