One-pot two-step tandem reactions for selective synthesis of pyrrolo[2,1-a]isoquinolines and dihydro-, tetrahydro-derivatives |
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Authors: | Ying HanHong Hou Qin FuChao-Guo Yan |
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Affiliation: | College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China |
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Abstract: | A sequential one-pot two-step tandem reaction for selective and efficient synthesis of pyrrolo[2,1-a]isoquinoline and its dihydro- and tetrahydro-derivatives has been developed. The tandem reactions of isoquinoline, α-halogenated methylene compounds, aromatic aldehydes, and cyanoacetamide firstly give tetrahydropyrrolo[2,1-a]isoquinolines as main products. The corresponding pyrrolo[2,1-a]isoquinolines and dihydropyrrolo[2,1-a]isoquinolines can be obtained directly by controlling oxidation with DDQ. The mechanism of this tandem reaction involved the 1,3-dipolar cycloaddition of isoquinolinium ylide as the key step. A unique elimination of the amido group preferring to the cyano group has been observed. |
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Keywords: | Heterocycles Azaaromatic N-ylide Isoquinoline Pyrrolo[2,1-a]isoquinoline One-pot reaction Tandem reaction |
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