One-Pot Synthesis of (E)-2-(3-Oxoindolin-2-ylidene)-2-arylacetonitriles

Аксенов, Н. А.; Аксенов, А. В.; Kurenkov, Igor A.; Kirillov, Nikita K.; Аксенов, Дмитрий А.; Arutiunov, Nikolai A.; Aksenova, Daria S.; Rubin, Michael

doi:10.3390/molecules27092808

Cited by 3 publications

(11 citation statements)

References 28 publications

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“…The plausible mechanism includes a double, domino-type Michael addition of a cyanide ion followed by sequential ring closing/opening steps to give, eventually, the corresponding 3-amino-4-het(aryl) maleimide derivatives in generally good yields. Conceptually, this transformation is related to the previously reported reactions of 2′-nitrochalcones with KCN, where depending on the conditions, either indolin-3-one 6 or 1-tetralone and 1-indanone 10 derivatives are formed.…”

Section: Discussionmentioning

confidence: 54%

“…24 In this regard, we believe that the practical, low-cost procedure towards α-amino-β-arylmaleimides described herein would be a valuable addition to the existing methods, enhancing greatly the scope of available compounds of this class. The featured reaction was discovered while working on the previously reported 6 transformation of 2′-nitrochalcone 1a into ( E )-2-(3-oxoindolin-2-ylidene)-2-phenylacetonitrile 2a (Scheme 3). Back then, the Michael addition of the cyanide ion was observed to proceed smoothly 25 at 30 °C in the presence of 1 equiv.…”

Section: Resultsmentioning

confidence: 98%

“…Eventually, we deciphered the structure of one of these products as ( E )-2-(3-oxoindolin-2-ylidene)-2-phenylacetonitrile 2a and found out the optimized conditions for its preparation. 6 Still, the nature of another compound, which was obtained as the major product after prolonged (approx. 2.5 h) heating at 80 °C, was not determined at that time.…”

Section: Resultsmentioning

confidence: 99%

“…We believe it is related to the synthesis of indolin-3-ones, described in our recent article. 6 First, the conjugate addition of KCN results in the formation of enolate 3 , which, eventually, transforms into 1-hydroxy-2-methyleneindolin-3-one 5 . At this stage, acidification accompanied by a subsequent reduction would lead to the formation of the aforementioned 3-indolinone-2-phenyl acetonitrile 2a .…”

Section: Resultsmentioning

confidence: 99%

“…The 2- and 2′-nitrochalcones, which are readily available via the Claisen–Schmidt condensation between the corresponding ortho -nitro acetophenones and benzaldehydes, 1 have long been a convenient starting point for the preparation of a wide range of heterocyclic compounds like pyrrolo[2,3- b ]quinolones, 1 quinoline N -oxides, 2 3-aminoindoles, 3 carbazoles, 4 benzothiophenes, 5 indolin-3-ones, 6 quinolines, 7 thioaurones, 8 sulphonamides 9 and tetralones 10 (Scheme 1). Herein, we would like to report an alternative, quite non-trivial domino-type transformation of 2′-nitrochalcones affording 4-(het)aryl-3-(2-carboxyanilino)maleimides (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

La Monica,

Alamia,

Bono

et al. 2024

Molecules

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Aurones, particular polyphenolic compounds belonging to the class of minor flavonoids and overlooked for a long time, have gained significative attention in medicinal chemistry in recent years. Indeed, considering their unique and outstanding biological properties, they stand out as an intriguing reservoir of new potential lead compounds in the drug discovery context. Nevertheless, several physicochemical, pharmacokinetic, and pharmacodynamic (P3) issues hinder their progression in more advanced phases of the drug discovery pipeline, making lead optimization campaigns necessary. In this context, scaffold hopping has proven to be a valuable approach in the optimization of natural products. This review provides a comprehensive and updated picture of the scaffold-hopping approaches directed at the optimization of natural and synthetic aurones. In the literature analysis, a particular focus is given to nitrogen and sulfur analogues. For each class presented, general synthetic procedures are summarized, highlighting the key advantages and potential issues. Furthermore, the biological activities of the most representative scaffold-hopped compounds are presented, emphasizing the improvements achieved and the potential for further optimization compared to the aurone class.

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The chemistry of heterocycles in the 21st century

Charushin,

Verbitskiy,

Chupakhin

et al. 2024

RUSS CHEM REV

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The chemistry of heterocyclic compounds has traditionally been and remains a bright area of chemical science in Russia. This is due to the fact that many heterocycles find the widest application. These compounds are the key structural fragments of most drugs, plant protection agents. Many natural compounds are also derivatives of heterocycles. At present, more than half of the hundreds of millions of known chemical compounds are heterocycles. This collective review is devoted to the achievements of Russian chemists in this field over the last 15–20 years. The review presents the achievements of leading heterocyclists representing both RAS institutes and university science. It is worth noting the wide scope of the review, both in terms of the geography of author teams, covering the whole of our large country, and in terms of the diversity of research areas. Practically all major types of heterocycles are represented in the review. The special attention is focused on the practical applications of heterocycles in the design of new drugs and biologically active compounds, high-energy molecules, materials for organic electronics and photovoltaics, new ligands for coordination chemistry, and many other rapidly developing areas. These practical advances would not be possible without the development of new fundamental transformations in heterocyclic chemistry.<br> Bibliography — 2237 references.

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One-Pot Synthesis of (E)-2-(3-Oxoindolin-2-ylidene)-2-arylacetonitriles

Abstract: A highly efficient and expeditious one-pot approach towards 2-(3-oxoindolin-2-yl)acetonitriles was designed, which involves a base-assisted aldol reaction of ortho-nitroacetophenones, followed by hydrocyanation, triggering an unusual reductive cyclization reaction.

Cited by 3 publications

References 28 publications

Synthesis of 2-carboxyaniline-substituted maleimides from 2′-nitrochalcones

Synthesis of 2-carboxyaniline-substituted maleimides from 2′-nitrochalcones

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

The chemistry of heterocycles in the 21st century

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