Synthesis of medium ring heterocycles using an intramolecular Heck reaction.
Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.
Department of Pharmaceutical Chemistry, University of California-San Francisco, 600 16th Street, San Francisco, California 94143-2280, USA.
Leggy A
LA
Arnold
Wenchen
W
Luo
R Kiplin
RK
Guy
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure
D006571:Heterocyclic Compounds; D007202:Indicators and Reagents