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Keywords = cyanoketones

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19 pages, 1834 KB  
Article
Synthesis of 3-(Quinazolin-4-yl)propionic Acids via an Acid-Catalyzed Rearrangement of 4-Oxobutyronitriles
by Nicolai A. Aksenov, Alexander E. Kurlikov, Alexander P. Barbolin, Polina S. Karaseva, Milena M. Baziyants, Elizabeth A. Glotova, Igor A. Kurenkov, Dmitrii A. Aksenov and Alexander V. Aksenov
Int. J. Mol. Sci. 2026, 27(9), 3903; https://doi.org/10.3390/ijms27093903 - 28 Apr 2026
Viewed by 470
Abstract
4-(2-Aminophenyl)-4-oxobutyronitriles in the presence of formic acid (HCOOH) and p-toluenesulfonic acid (TsOH) undergo an unusual rearrangement providing access to a range of 3-(quinazolin-4-yl)propionic acids that have been poorly represented in the literature, with only a few isolated examples known to date. The [...] Read more.
4-(2-Aminophenyl)-4-oxobutyronitriles in the presence of formic acid (HCOOH) and p-toluenesulfonic acid (TsOH) undergo an unusual rearrangement providing access to a range of 3-(quinazolin-4-yl)propionic acids that have been poorly represented in the literature, with only a few isolated examples known to date. The reaction demonstrates a new route to the quinazoline core through transfer of the nitrile group nitrogen, mediated through the formation of a pyrrolidine cycle. The availability of 4-oxobutyronitrile precursors—2′-aminochacones—provides high variability of substituents in the required positions of product. The transformation is general and can be extended to the preparation of 2-substituted 3-(quinazolin-4-yl)propionic acids through preliminary acylation or to the synthesis of 4-(quinazolin-4-yl)butyric acids. Full article
(This article belongs to the Section Physical Chemistry and Chemical Physics)
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12 pages, 1011 KB  
Article
The Synthesis of Novel aza-Steroids and α, β-Unsaturated-Cyanoketone from Diosgenin
by Dayana Mesa, Yarelys E. Augusto, Giselle Hernández, Juan P. Figueroa-Macías, Francisco Coll, Andrés F. Olea, María Núñez, Hernán Astudillo Campo, Yamilet Coll and Luis Espinoza
Molecules 2023, 28(21), 7283; https://doi.org/10.3390/molecules28217283 - 26 Oct 2023
Cited by 1 | Viewed by 3772
Abstract
Recent studies have demonstrated the antiproliferative and cytotoxic effects of aza-steroids and steroidal sapogenins on human cancer cell lines. The scientific community has shown a growing interest in these compounds as drug candidates for cancer treatment. In the current work, we report the [...] Read more.
Recent studies have demonstrated the antiproliferative and cytotoxic effects of aza-steroids and steroidal sapogenins on human cancer cell lines. The scientific community has shown a growing interest in these compounds as drug candidates for cancer treatment. In the current work, we report the synthesis of new diosgenin oxime derivatives as potential antiproliferative agents. From (25 R)-5α-spirost-3,5,6-triol (1), a diosgenin derivative, ketones 2, 3, 4, and 9 were obtained and used as precursors of the new oximes. A condensation reaction was carried out between the steroidal ketones (2, 3, 4, and 9) with hydroxylamine hydrochloride in 2,4,6-trimethylpyridine to produce five spirostanic oximes (four of them are not reported before) with a 42–96% yield. Also, a new spirostanic α, β-unsaturated cyanoketone was synthesized via Beckmann fragmentation using thionyl chloride with a 62% yield. Furthermore, we proposed a reaction mechanism with the aim of explaining such transformation. Full article
(This article belongs to the Section Organic Chemistry)
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12 pages, 6577 KB  
Article
Global Search for Stable C4H5NO Compounds—Guinness Molecules and Stability Islands
by Oleg A. Mikhaylov and Ilya D. Gridnev
Molecules 2023, 28(2), 728; https://doi.org/10.3390/molecules28020728 - 11 Jan 2023
Viewed by 2370
Abstract
Global reaction route mapping (GRRM) analysis for compounds with the formula C4H5NO allowed for the detection of the corresponding “Guinness molecules” 000 and 001, as well as around 150 other stable minima of the same composition. The results [...] Read more.
Global reaction route mapping (GRRM) analysis for compounds with the formula C4H5NO allowed for the detection of the corresponding “Guinness molecules” 000 and 001, as well as around 150 other stable minima of the same composition. The results suggest that compounds of similar functionality form a kind of “Stability Island” with their free energies of formation falling within s relatively limited range. Full article
(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)
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9 pages, 2049 KB  
Article
Three-Component Condensation of β-Ketonitriles, 4-Fluorobenzaldehyde, and Secondary Cyclic Amines
by Dmitry V. Osipov, Kirill S. Korzhenko and Vitaly A. Osyanin
Reactions 2022, 3(4), 625-633; https://doi.org/10.3390/reactions3040042 - 12 Dec 2022
Cited by 1 | Viewed by 5421
Abstract
A new three-component condensation of β-ketonitriles, 4-fluorobenzaldehyde, and secondary cyclic amines was developed. A possible reaction mechanism has been proposed including Knoevenagel condensation followed by aromatic nucleophilic substitution. It was found that in the case of 3-oxopropanenitrile bearing the 6-amino-1,3-dimethyluracil moiety, the reaction [...] Read more.
A new three-component condensation of β-ketonitriles, 4-fluorobenzaldehyde, and secondary cyclic amines was developed. A possible reaction mechanism has been proposed including Knoevenagel condensation followed by aromatic nucleophilic substitution. It was found that in the case of 3-oxopropanenitrile bearing the 6-amino-1,3-dimethyluracil moiety, the reaction is not accompanied by fluorine substitution in the Knoevenagel adduct, and the Michael addition of a secondary amine occurs followed by oxidation. Full article
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