title: [Efficient construction of nitrogen-containing heterocycles utilizing CN functional groups and its application to the synthesis of natural products].
abstract: Viridicatin derivatives were synthesized from cyanoacetanilides utilizing the CN groups as electron-withdrawing groups and leaving groups. Also, the key scaffolds of glycocitlones were constructed via the intramolecular Houben-Hoesch-type reactions of cyanoacetanilides where the CN groups functioned as electrophiles. It was found that Houben-Hoesch-type reactions of cyanoacetanilides were promoted by α-functionalization such as perfluoroacylation and N,N-dimethylaminomethylenation and that introduction of such substituents at α-position with respect to the CN groups greatly influenced the physical properties and chemical reactivity of the CN groups.
authors: School of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya, Hyogo, Japan. ykoba@mukogawa-u.ac.jp
authors: Yusuke
authors: Y
authors: Kobayashi
mesh_terms: D000083:Acetanilides / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis*; D003500:Cyclization; D004583:Electrons; D006571:Heterocyclic Compounds; D006912:Hydroxyquinolines / Q000138:chemical synthesis*; D009570:Nitriles / Q000737:chemistry*; D009584:Nitrogen; D055601:Organic Chemistry Phenomena; D015363:Quinolones
chemical_list: D000083:Acetanilides; D001688:Biological Products; D006571:Heterocyclic Compounds; D006912:Hydroxyquinolines; D009570:Nitriles; D015363:Quinolones; C009673:viridicatin; D009584:Nitrogen