Study On Selectivecontrol Efficient Synthetic Quinoline Derivatives Based On Tandem Reaction

Quinoline derivatives are unique nitrogen-containing heterocycles that have attracted particular attention due totheir special place as building blocks in natural products,pharmaceutical agents, and materials. Based on progress in synthesis of quinoline in recent years, the paper was compose of two parts which was to selective synthesis of quinoline derivatives. The first part of this paper focuses on L-proline controlling selective synthesis of 2,3-dihydrothieno(2,3-b)quinolines and thieno(2,3-b)-quinolines, The second part was about quinine derivatives catalyzedsynthesis ofthiopyrano[2,3-b]quinolinederivatives with optical activity.In the current work, a series of 4H-3,1-benzothiazinedericatives were synthesized via the domino reaction of o-isothiocyanato-(E)-cinnamaldehyde and secondaryamine. Meanwhile,We found an unexpected domino AMBH/alkylation/aldol reactionofo-isothiocyanato-(E)-cinnamaldehydes with a-halocarbonylcompounds, catalyzed by L-proline. This dominoreaction could be applied tosynthesis of 2,3-dihydrothieno(2,3-b)quinolines and Thieno(2,3-b)-quinolines. The absolute configurations were determined by the single-crystal X-ray analysis.In addition.2-mercaptoquinoline-3-carbaldehyde were synthesized viaintramolecular AMBH reaction of o-isothiocyanato-(E)-cinnamaldehyde. 3.4-dihydro-2H-thiopyrano[2.3-b]quinoline was synthesized via the Micheal/Cyclization domino reaction of 2-mercaptoquinoline-3-carbaldehyde and nitroolefin. Withing the of various reaction conditions studied, we found Id and Ihcouldeffective catalyze the reaction and had excellent yield, enantioselectiveand the diastereoselective. The most important thing is that the productswith two kinds of catalysts were different configurations, were a pair of the diastereomer. Two absolute configurations were determined by the single-crystal X-ray analysis.