[1,5]-Hydride Transfer/Cyclization of ortho-Amino Alkynyl Fischer Carbene Complexes: A Useful Tool for the Synthesis of Quinoline Derivatives

✍ Scribed by José Barluenga; Martín Fañanás-Mastral; Amadeo Fernández; Fernando Aznar

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 304 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201001717

✦ Synopsis

Abstract

An efficient method for the synthesis of compounds containing a quinoline moiety by using o‐aminophenyl alkynyl Fischer carbene complexes as starting materials is described. The reaction is based on a cascade process involving [1,5]‐hydride transfer/cyclization to afford new alkenylcarbene complexes with quinoline moiety 2. The reaction of alkenyl complexes 2 with unsaturated substrates such as electron‐poor alkynes afford furo[2′,3′‐3,4]cyclopenta[1,2‐c]quinolinone derivatives 6 and (1,2‐dihydroquinolin‐3‐ylvinyl)malonates 12 when propiolic aldehydes and propiolates are used, respectively. The reactivity of the alkenylcarbene complexes was also studied by using 1,3‐dienes to afford cyclohepta[c]quinolinones 17 when Danishefsky's diene is used and 3‐pirimidinylquinoline derivatives 21 when 4‐amino‐1‐azadienes are employed.