Several a-spirocyclopropanated heterocyclic ketones were converted to the corresponding cyclopentene-anellated heterocycles in moderate to good yields (overall 31-60%) by Wadsworth- Emmons olefination followed by thermal rearrangement of the formed vinylcyclopropanes. In this sequence, the phosphonoacetonitrile was found to be superior to phosphonoacetate in the Wadsworth- Emmons olefinations of tetrahydropyridones.
Cyclopentene Anellation on Assorted Heterocyclic Skeletons byVinylcyclopropane Rearrangement / A. Brandi; S. Cicchi; M. Brandl; S. I. Kozhushkov; A. de Meijere. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 2001:(2001), pp. 433-435.
Cyclopentene Anellation on Assorted Heterocyclic Skeletons byVinylcyclopropane Rearrangement
BRANDI, ALBERTO;CICCHI, STEFANO;
2001
Abstract
Several a-spirocyclopropanated heterocyclic ketones were converted to the corresponding cyclopentene-anellated heterocycles in moderate to good yields (overall 31-60%) by Wadsworth- Emmons olefination followed by thermal rearrangement of the formed vinylcyclopropanes. In this sequence, the phosphonoacetonitrile was found to be superior to phosphonoacetate in the Wadsworth- Emmons olefinations of tetrahydropyridones.
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