A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

Abstract

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Ring‐Closing Metathesis: Novel Routes to Aromatic Heterocycles

“…The group also applied this procedure to the synthesis of quinolines 114 and 117, which are intermediates in the synthesis of the anti-malarial agents quinine [60] and phenyl-2-palmitoylamino-3-morpholino-1-pro- [61] respectively (Scheme 26). [61,62] The Bennasar group used a similar strategy to construct quinolines with the elegant use of the enamide-ene RCM reaction (Scheme 27).…”

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.…”

“…Formal synthesis of chloroquine, chinine, PPMP-quinine hybrid 21) : Encouraged by these results, we applied this novel method to the synthesis of key intermediates of antimalarial agents, such as quinine, [88][89][90][91][92] chloroquine, 93,94) and PPMP-quinine hybrid, 87) which are shown in Chart 7.…”

TMSCl-Catalyzed synthesis of substituted quinolines from arylimines and enolizable aldehydes

“…Recently, more and more new simple and elegant syntheses of substituted quinolines have been described. [25][26][27][28][29][30][31][32][33][34][35][36][37][38] Among these methods, the procedure using a HCl-DMSO system seems to be a very practical method for substituted quinolines starting from imines and carbonyl compounds. 34 In view of the remarkable importance from the pharmacological, industrial and synthetic point, the development of new synthetic approaches using mild reaction conditions remains an active research field.…”