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[1,5]‐Hydride Transfer/Cyclization of ortho ‐Amino Alkynyl Fischer Carbene Complexes: A Useful Tool for the Synthesis of Quinoline Derivatives
Author(s) -
Barluenga José,
FañanásMastral Martín,
Fernández Amadeo,
Aznar Fernando
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001717
Subject(s) - chemistry , moiety , quinoline , carbene , hydride , reactivity (psychology) , medicinal chemistry , combinatorial chemistry , alkyne , diene , stereochemistry , organic chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology , hydrogen
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.