Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes
Publication type: Journal Article
Publication date: 2008-01-10
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency of the process, and increased the scope of the aromatic aldehydes. Incorporating water as the catalyst in ethanol for the condensation step allows stoichiometric amounts of malononitrile and aldehyde to be employed. The reduction step takes place quickly and efficiently with sodium borohydride to give monosubstituted malononitriles via filtration or extraction. The product from 2-quinolinecarboxaldehyde quickly rearranges to a novel indolizine, while alkylation of the monosubstituted derivative provides an unsymmetrically disubstituted malononitrile that does not rearrange.
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Total citations:
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Citations from 2025:
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Sammelson R. et al. Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes // Synthesis. 2008. Vol. 2008. No. 2. pp. 279-285.
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Sammelson R., Tayyari F., Wood D., Fanwick P. Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes // Synthesis. 2008. Vol. 2008. No. 2. pp. 279-285.
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RIS
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TY - JOUR
DO - 10.1055/s-2007-990945
UR - https://doi.org/10.1055/s-2007-990945
TI - Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes
T2 - Synthesis
AU - Sammelson, Robert
AU - Tayyari, Fariba
AU - Wood, Dwight
AU - Fanwick, Phillip
PY - 2008
DA - 2008/01/10
PB - Georg Thieme Verlag KG
SP - 279-285
IS - 2
VL - 2008
SN - 0039-7881
SN - 1437-210X
ER -
Cite this
BibTex (up to 50 authors)
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@article{2008_Sammelson,
author = {Robert Sammelson and Fariba Tayyari and Dwight Wood and Phillip Fanwick},
title = {Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes},
journal = {Synthesis},
year = {2008},
volume = {2008},
publisher = {Georg Thieme Verlag KG},
month = {jan},
url = {https://doi.org/10.1055/s-2007-990945},
number = {2},
pages = {279--285},
doi = {10.1055/s-2007-990945}
}
Cite this
MLA
Copy
Sammelson, Robert, et al. “Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes.” Synthesis, vol. 2008, no. 2, Jan. 2008, pp. 279-285. https://doi.org/10.1055/s-2007-990945.