Convenient access to isoindolinones via carbamoyl radical cyclization. Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products

An efficient and convenient access to 2- tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its...

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Bibliographic Details
Published in:Tetrahedron 2011-04, Vol.67 (14), p.2693-2701
Main Authors: López-Valdez, Germán, Olguín-Uribe, Simón, Millan-Ortíz, Alejandra, Gamez-Montaño, Rocio, Miranda, Luis D.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Natural products
Organic chemistry
Peroxides
Preparations and properties
Radicals
Reactivity and mechanisms
Synthesis (chemistry)
Tetrahedrons
Transformations
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Description
Summary:An efficient and convenient access to 2- tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Additionally, the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.01.003