Domino Michael–O-alkylation: one-pot synthesis of dialkyl 4-oxo-2,3-dihydro-2,3-furandicarboxylates

The KSCN-catalyzed reaction of dialkyl acetylenedicarboxylates with pentane-2,4-dione in acetone, led to dialkyl 2-(1-acetyl-2-oxopropyl)-2-butenedioates in excellent yields. When these reactions were carried out in MEK (butane-2-one), dialkyl 4-oxo-2,3-dihydro-2,3-furandicarboxylates were obtained...

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Bibliographic Details
Published in:Molecular diversity 2011-05, Vol.15 (2), p.451-456
Main Authors: Yavari, Issa, Sirouspour, Mehdi, Souri, Sanaz
Format: Article
Language:English
Subjects:
Alkylation
Biochemistry
Biomedical and Life Sciences
Catalysis
Chemical reactions
Chemical synthesis
Chemistry - methods
Full-Length Paper
Furans - chemical synthesis
Life Sciences
Molecular structure
Organic chemicals
Organic Chemistry
Pharmacy
Polymer Sciences
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Summary:The KSCN-catalyzed reaction of dialkyl acetylenedicarboxylates with pentane-2,4-dione in acetone, led to dialkyl 2-(1-acetyl-2-oxopropyl)-2-butenedioates in excellent yields. When these reactions were carried out in MEK (butane-2-one), dialkyl 4-oxo-2,3-dihydro-2,3-furandicarboxylates were obtained exclusively. This difference in reactivity is discussed in terms of the possibility of cationic exchange in butane-2-one. Graphical Abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-010-9265-2