Ring Enlargement versus Selenoetherification on the Reaction of Allenyl Oxindoles with Selenenylating Reagents

Lactam-tethered allenols, readily prepared from α-oxolactams, were used as starting materials for divergent reactivity with selenenylating reagents. Either oxycyclization (spirocyclic selenolactams) or ring expansion (selenoquinolones) can be achieved through the choice of both reagents and substrat...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-04, Vol.77 (7), p.3549-3556
Main Authors: Alcaide, Benito, Almendros, Pedro, Luna, Amparo, Gómez-Campillos, Gonzalo, Torres, M. Rosario
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Catalysis
Chemical reactivity
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Humans
Indicators and Reagents - chemistry
Indoles - chemistry
Kinetics and mechanisms
Lactams - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Selenium Compounds - chemistry
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Summary:Lactam-tethered allenols, readily prepared from α-oxolactams, were used as starting materials for divergent reactivity with selenenylating reagents. Either oxycyclization (spirocyclic selenolactams) or ring expansion (selenoquinolones) can be achieved through the choice of both reagents and substrates. The biological activity of some of the synthesized heterocycles has additionally been evaluated in four human cancer cell lines.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo202495z