An efficient and improved synthesis of 1,5-diketones: versatile conjugate addition of nucleophiles to α,β-unsaturated enones and alkynones

Several 1,5-diketones have been prepared in good to excellent yields by versatile conjugate addition of nucleophiles such as cyclic or acyclic ketones, amines and thiols to α,β-unsaturated enones and alkynones, in the presence of catalytic amounts of 10% aq NaOH, TBAI and DMSO at ambient temperature...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 18; pp. 3077 - 3079
Main Authors Shankar, Ravi, Jha, Ashok K., Singh, Uma Sharan, Hajela, K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.05.2006
Elsevier
Subjects
1,5-Diketones
Alkynones
Chemistry
Chemistry, Organic
Conjugate addition
Physical Sciences
Science & Technology
α,β-Unsaturated enones
α,β-Unsaturated enones
Conjugate addition
Alkynones
1,5-Diketones
KETONES
AMINES
alkynones
alpha,beta-unsaturated enones
ALPHA,BETA-ETHYLENIC COMPOUNDS
conjugate addition
INDOLES
MERCAPTANS
1,5-diketones
MICHAEL ADDITION
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Summary:Several 1,5-diketones have been prepared in good to excellent yields by versatile conjugate addition of nucleophiles such as cyclic or acyclic ketones, amines and thiols to α,β-unsaturated enones and alkynones, in the presence of catalytic amounts of 10% aq NaOH, TBAI and DMSO at ambient temperature. The choice of solvent and phase-transfer catalyst played a critical role in improving the reaction rate and yields of the products.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.03.008