Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

The condensation of 5-alkoxycarbonyl-1H-pyrrolediones with cyclic ketazinones was systematically investigated. It was discovered that the regioselectivity of this reaction can be easily swapped between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane....

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2017-10, Vol.13 (1), p.2179-2185
Main Authors: Dubovtsev Alexey Yu, Dmitriev, Maksim V, Maslivets, Аndrey N, Rubin, Michael
Format: Article
Language:English
Subjects:
Chemistry
Condensation
Crystal structure
Crystallography
Full Research Paper
Hydrogenation
Indoles
nitrogen heterocycles
oxygen heterocycles
pyrrolediones
spiro compounds
synthetic methods
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Summary:The condensation of 5-alkoxycarbonyl-1H-pyrrolediones with cyclic ketazinones was systematically investigated. It was discovered that the regioselectivity of this reaction can be easily swapped between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane. The control of this regioselectivity is efficiently governed by steric effects at the hydrazone moiety of the ketazinone reagent.
ISSN:2195-951X
1860-5397
1860-5397
DOI:10.3762/bjoc.13.218