Based On The Synthesis Of 2,3-Dibromo Propylene Instead Of Nitrogen,the Preparation And Characterization Of Heterocyclic Compounds

The synthesis and application of nitrogen-containing heterocyclic compounds are one of the hotspots in organic synthesis research.Synthesis of materials science,medicine as well as biology based on tetrahydrothiazole-2-thione and[1,2,3]triazole-[1,5-?]pyrazine have been widely used in many fields,especially[1,2,3]triazole-[1,5-?]pyrazine,in the past two years,in a PARP inhibition,it has played a crucial role in the synthesis of fluazapril.In view of this,shortening the reaction process and seeking a mild synthetic condition is the direction of future organic synthesis workers' concerns and efforts.In this paper,two novel methods for the construction of nitrogen-containing heterocyclic rings with 2,3-dibromopropene are proposed:(1)2,3-dibromopropene,carbon disulfide and primary amine compounds are subjected to three-component one-pot reaction.4-dibromopropene,3-bromopropyne,primary amine and sodium azide were obtained by the following procedure: [1,2,3]triazole-[1,5-?]pyrazine is an important pharmaceutical intermediate compound that greatly exerts the reactivity of 2,3-dibromopropene with primary amines to a certain extent.And a novel method for the preparation of isoxazole to obtain novel isoxazoles.The main work of the paper is as follows:1,with 2,3-dibromopropene and primary amine as raw materials,in isopropanol solvent,and carbon disulfide at room temperature occurred in three component ring addition reaction,synthesis of a series of stable and novel tetrahydrothiazole-2-thioketone compounds,providing excellent properties for materials and biology intermediates.Compared with the past,the method has the advantages of simple steps,high yield,mild reaction condition and good selectivity.2,to 2,3-dibromopropene and primary amine as raw materials,first to obtain N-(2-bromo-allyl)aniline compounds.Followed by reaction with 3-bromopropyne using potassium carbonate as a catalyst to give N-(2-bromoallyl)-N-propargylanilide.Finally,in the CuI / K2CO3 catalytic system,with the sodium azide ring off the reaction [1,2,3]triazole-[1,5-?]pyrazine compounds this important pharmaceutical intermediates.3,3-Bromo-1-phenylbut-3-en-1-ol was obtained in the Sn/HCl catalytic system using 2,3-dibromopropene and aromatic aldehyde as starting materials.Propyne,withthe participation of NaH to give the [3-bromo-1-(prop-2-yn-1-yloxy)but-3-en-1-yl]benzene compound.And it finally reacted with a previously prepared acetaldehyde oxime in the presence of triethylamine to give 3-phenyl-5-{2-phenyl-2-[(3-phenylisoxazol-5-yl)Oxy] ethyl} isoxazole compounds.