Development of novel reactions using ruthenium carbene catalyst and its application to novel methods for preparing nitrogen-containing heterocycles

Ring‐Closing Metathesis: Novel Routes to Aromatic Heterocycles

“…[61,62] The Bennasar group used a similar strategy to construct quinolines with the elegant use of the enamide-ene RCM reaction (Scheme 27). [53] The formation of two quinolines 120 and 123 was reported, whereby the oxidation of the 1,4-dihydroquinoline system was effected using catalytic palladium on carbon under an atmosphere of oxygen.…”

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

“…For more than ten years, we have been exploring a synthetic methodology for nitrogen-containing heterocycles using these ruthenium carbene catalysts and applying them to the synthesis of biologically active natural products. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] Here, we describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis and selective isomerization of terminal olefin, and its application to the synthesis of the natural products, (Ϫ)-coniceine, (S)-pyrrolam A and angustureine.…”

“…Axially Chiral Macrolactams 14,17) : We recently reported that new axially chiral ligands, 1,1Ј-(2,2Ј-bisacylamino)binaphthalenes (BINAMIDE), are effective in the ytterbium-catalyzed asymmetric Diels-Alder reaction between cyclopentadiene and crotonyl-1,3-oxazolidin-2-one (Chart 4). 53) 1,1Ј-(2,2Ј-Bisacylamino)binaphthalenes (23)(24)(25) were synthesized by reacting binaphthyldiamine with mixed anhydride of the corresponding acid, and then reacting the product with ruthenium carbene catalyst (D) under various conditions (Table 4).…”

A Ruthenium‐Catalyzed Approach to the Friedländer Quinoline Synthesis

“…Ruthenium complexes catalyze the reaction of aniline with allyl alcohols,10 triallylamines,11 allylammonium chlorides11 and even alkylamines 12. Substituted quinolines were synthesized by Arisawa, Theeraladanon et al via ring closing metathesis of α,ω‐dienes derived from 2‐isopropenylaniline 13–15. Other researchers reported the use of Pd,16–19 Ni,20 Rh,21,22 and Co23,24 complexes for transition‐metal mediated quinoline synthesis.…”