Chemistry of pyrrolizines; reactions with cyanogen bromide and trifluoroacetic anhydride

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Verboom, W. and Visser, G.W. and Reinhoudt, D.N. (1982) Chemistry of pyrrolizines; reactions with cyanogen bromide and trifluoroacetic anhydride. Tetrahedron, 38 (2). pp. 1831-1835. ISSN 0040-4020

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Abstract:Interaction of the pyrrolizine 3 with cyanogen bromide in a tetrahydrofuran/water mixture affords addition to the enamine double bond with formation of 5 which can be aromatized to 6 by silica gel. Reaction of 6 with cyanogen bromide in the same solvent mixture yields the indoline 8a which structure is proved in a chemical way by conversion of the product into the aldehyde 8d. The different reaction pathway is discussed in terms of steric hindrance by the ester groups. Treatment of 6 with trifluoroacetic anhydride gives the trifluoroacetylated compound 11. Removal of the sterically hindered ester groups in 6, with acetic acid in quinoline at 200°, is accompanied by the simultaneous decarboxylation to yield the pyrrolo[1,2-a]indole 13
Item Type:Article
Copyright:© 1982 Elsevier Science
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/68995
Official URL:http://dx.doi.org/10.1016/0040-4020(82)80259-7
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