Journal
TETRAHEDRON
Volume 67, Issue 12, Pages 2313-2322Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.01.046
Keywords
Heterocycles; Azaaromatic N-ylide; Isoquinoline; Pyrrolo[2,1-a]isoquinoline; One-pot reaction; Tandem reaction
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Funding
- National Natural Science Foundation of China [20972132]
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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, a-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. (C) 2011 Elsevier Ltd. All rights reserved.
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