One-pot Synthesis Of Methylthio Arylbutenynes

Methylthio arylbutenynes include aromatic ring, double bond, triple bond andhighly active methylthio groups. If the reaction sites were treated with differentreagents, various types of compounds can be obtained. Therefore, Methylthioarylbutenynes are important synthetic intermediates. Because of their containingsulfur atoms, methylthio arylbutenynes have a promising future in material andself-assembly aspects. And their application in anticancer antibiotics largely dependon containing conjugated enyne groups, which is the core structure of manyantitumour antibiotics. So, it is necessary for us to find a simple and convenientmethod to synthetize methylthio arylbutenynes both theoretically and practically.After reviewing a plentiful of literature and the research results of our laboratoryin the foretime, the author design a new one-pot reaction using aryl aldehyde as thestarting material to synthesize methylthio arylbutenyne by means of aldol reaction,α-bromination, nucleophilic substitution and elimination. Compared with the previousmethods, the one-pot reaction uses less substrate and can be handled more easily，withgood versatile.The main content of this paper is as follows:In the first chapter, Various reactions for construction of methylthio arylethynesand conjugated enynes and the application of some target moleculars were firstlysubjected to review. On its base, the author determined the content of this paper, andrevealed its significance.In the second chapter of this paper, the one-pot reaction substrates were prepared.the author used aryl aldehyde as our raw material. By means of aldol reaction,α-bromination, nucleophilic substitution, we got a series of methylthio arylbutenone.The mechanism, procedure, and spectras of all this were also discussed.In the last chapter of this paper, the author got the target compounds throughone-pot elimination. At the same time, the one-pot method was compared to otherprocess invoving conversion of carbonyl compounds to alkynes. Also, The mechanism,procedure,and spectras of all this were studied.All of the intermediates and target compounds in this paper have beendeterminated by¹H NMR,¹³C NMR, IR and MS.