Diversity-oriented synthesis of 3-iodochromones and heteroatom analogues via ICl-induced cyclization.
The ICl-induced cyclization of heteroatom-substituted alkynones provides a simple, highly efficient approach to various 3-iodochromones and analogues. This process is run under mild conditions, tolerates various functional groups, and generally provides chromones in good to excellent yields. Subsequent palladium-catalyzed transformations afford a rapid increase in molecular complexity and a convenient preparation of a wide range of functionally substituted chromones, furans, and polycyclic compounds. Iodothiochromenones and iodoquinolinones are also prepared by similar ICl-induced cyclizations.
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Chengxiang
C
Zhou
Anton V
AV
Dubrovsky
Richard C
RC
Larock
D002384:Catalysis; D002867:Chromones / Q000138:chemical synthesis*; D003500:Cyclization; D017613:Iodine Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D010165:Palladium
D002867:Chromones; D017613:Iodine Compounds; D007659:Ketones; D010165:Palladium