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Title
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Three component reaction between 4-toluenesulfonylmethyl isocyanid and 1,3-diketones in the presence of acetylenic esters in polyethylene glycol (PEG):A convenient synthesis of highly functionalized 2-amino-4H-pyranes
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Type
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Presentation
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Keywords
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PEG , acyclic 1,3-diketones , 2-amino-4H-pyranes
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Abstract
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Oxygen heterocyclic compounds occupy an important position in natural product chemistry. They occur in plant life, most notably as flavenoids, and in marine environment where they form a part of the wide range of macrocyclic molecules. The presence of oxacyclic units in polyether and macrolide antibiotics has stimulated intense synthetic activity in pyran chemistry because of the significant pharmacological activity shown by these systems. Substituted 2-amino-4H-pyrans are significant in a number of practical applications. Some have been shown to exhibit biological activity [2] and they also serve as convenient starting materials for synthesis of condensed heterocycles [2]. Recently, the use of polyetylenglycol (PEG) as solvent has attracted much attention in the context of green synthesis [3]. We previously reported [4, 5] reactions between cyclic and acyclic 1,3-diketones and alkyl isocyanides with acetylenic esters to produce 2-amino-4H-pyrane derivatives. In the present work it will be shown that a on-pot three component reaction can produce the desired substituted 2-amino-4H-pyrans in good yield by the reaction of 4-toluenesulfonylmethyl isocyanid and 1,3-diketones in the presence of acetylenic esters in PEG as solvent.
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Researchers
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Farough Nasiri (Second Researcher), Amin Zolali (First Researcher)
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