A three-component condensation of cyclic enamino ketones, phenylglyoxal hydrate, and ethyl cyanoacetate

Andin, A. N.

doi:10.1007/s10593-021-02863-0

Cited by 6 publications

(4 citation statements)

References 9 publications

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“…Therefore, the reactions of enamines with different biselectrophiles have been investigated extensively for the construction of nitrogen‐containing heterocycles [25] . One of the most important and famous enamines for the synthesis of nitrogen‐containing heterocycles is nitroketen aminals, [26] cyclic enamino ketones, [27] and α‐ aminomaleimides, [28] which played an important role in this process. According to our knowledge, the three‐component reaction of 2‐chloroquinoline‐3‐carbaldehydes, malononitrile derivatives and enamines such as nitroketen aminals, cyclic enamino ketones to synthesize quinoline‐based pyrido[1,2‐ a ]pyrimidines/imidazo[1,2‐ a ]pyridines [29] and N ‐arylamino biquinoline derivatives have been previously reported [16] .…”

Section: Resultsmentioning

confidence: 99%

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Efficient Synthesis of Highly Substituted N‐Arylamino quinolone‐based Pyrrolo[3,4‐b]pyridines and Pyrazolone‐based Pyrrolo[3,4‐b]pyridines Through a One‐Pot Three‐Component Reaction

Alizadeh,

Moterassed,

Rostampoor

2023

ChemistrySelect

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In this research, a simple and efficient strategy for the straightforward synthesis of multisubstituted N-arylamino quinolone-based pyrrolo [3,4-b]pyridine derivatives and pyrazolone-based pyrrolo [3,4-b]pyridine derivatives is presented by a sequential three-component reaction of α-aminomaleimides, 2chloroquinoline-3-carbaldehyde/5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and malononitrile/ethyl 2-cyanoacetate as readily available starting materials in EtOH at room temperature. The merit of this sequential Michael addition/ intramolecular cyclization is highlighted by its high energy conserving (short reaction times at room temperature) excellent yields, metal-free catalyst, and green and mild conditions in a one-pot reaction. With this synthesis, group-assistantpurification (GAP) chemistry can be simplified by eliminating chromatography and recrystallization, and the pure products can be obtained by washing the crude products with 95 % ethanol. Their structures were characterized by spectroscopic data IR, MS, 1 H, and 13 C NMR analysis.

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Section: Resultsmentioning

confidence: 99%

“…Based on our previous experiences [27] and the study of published articles on the reaction of 2‐chloroquinoline‐3‐carbaldehyde with active methylene compounds, we conducted the first experiment in ethanol solvent at room temperature. Fortunately, no further optimization was required, as the products were isolated in 77–92 % yield.…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of Highly Substituted N‐Arylamino quinolone‐based Pyrrolo[3,4‐b]pyridines and Pyrazolone‐based Pyrrolo[3,4‐b]pyridines Through a One‐Pot Three‐Component Reaction

Alizadeh,

Moterassed,

Rostampoor

2023

ChemistrySelect

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“…Andin 65 described a three-component condensation of cyclic enaminones 111, phenylglyoxal hydrate (114a), and ethyl cyanoacetate in EtOH leading to the formation of functionalized 2,3,4,5,6,7-hexahydro-(117) and 4,5,6,7-tetrahydroindoles 118 and 119 (Scheme 31). The corresponding intermediates, 2,3,4,5,6,7-hexahydroindoles 117a,b, are formed under mild conditions.…”

Section: Reaction Of -Enaminones With Vinyl Ethersmentioning

confidence: 99%

“…Optional mechanism 2 does not agree with the fact that compounds 118 (R = Bn, Ar) are converted into tetrahydroindolylacetonitriles 119 upon heating under reflux in DMF (Scheme 32b). 65 Kolos et al 66 reported also a series of functionalized tetrahydroindol-4-one derivatives by a reaction of cyclic enaminones with arylglyoxal hydrates using -dicarbonyl compounds instead of ethyl cyanoacetate by the above strategy.…”

Section: Review Synthesismentioning

confidence: 99%

Recent Advances in the Synthesis of Indoles with Partially Hydrogenated Benzene Ring (Tetrahydroindoles)

Mamedov,

Zhukova

2023

Synthesis

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In this review, a fragmentary analysis of 4,5,6,7-tetrahydroindoles was performed and, on its basis, the existing methods of their synthesis published over the past 15 years have been summarized, and analyzed, as well as, if necessary, an analysis of earlier works is carried out. The proposed reaction mechanism is considered, as well as factors that significantly influence the course of the process. Among such factors: temperature, type and content of the catalyst, promoting additives, method of the process, etc. Particular attention is paid to fundamentally new methods that make it possible to synthesize various derivatives of the mentioned heterocyclic systems from available and cheap reagents, and in some cases under environmentally benign conditions.1 Introduction2 Intramolecular Reactions Leading To Tetrahydroindoles2.1 Ring Closure Reactions with N–C2 Bond Formation (a)2.2 Ring Closure Reactions with C2–C3 Bond Formation (b)2.3 Ring Closure Reactions with C3–C3a Bond Formation (c)2.4 Ring Closure Reactions with C7a–N Bond Formation (e)2.5 Ring Closure Reactions with C4–C5 Bond Formation (g)2.6 Ring Closure Reactions with C3a–C4 Bond Formation (h)3 Intermolecular Reactions Leading To Tetrahydroindoles3.1 Ring Closure Reactions with N–C2 + C3–C3a Bond Formation (ac)3.2 Ring Closure reactions with N–C2 + C7a–N Bond Formation (ae)3.3 Ring Closure reactions with C3–C3a + C7a–N Bond formation (ce)3.4 Ring Closure Reactions with N–C2, C3–C3a, and C7a–N Bond Formation (ace)4 Recovery Processes (Hydrogenation) of Indoles and Oxidation of Perhydroindoles in the Synthesis of 4,5,6,7-Tetrahydroindoles5 Conclusion

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Synthesis of 3-substituted tetrahydroindol-4-one

Kolos

Marchenko

Chechina

et al. 2021

Chem Heterocycl Comp

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A three-component condensation of cyclic enamino ketones, phenylglyoxal hydrate, and ethyl cyanoacetate

Cited by 6 publications

References 9 publications

Efficient Synthesis of Highly Substituted N‐Arylamino quinolone‐based Pyrrolo[3,4‐b]pyridines and Pyrazolone‐based Pyrrolo[3,4‐b]pyridines Through a One‐Pot Three‐Component Reaction

Efficient Synthesis of Highly Substituted N‐Arylamino quinolone‐based Pyrrolo[3,4‐b]pyridines and Pyrazolone‐based Pyrrolo[3,4‐b]pyridines Through a One‐Pot Three‐Component Reaction

Recent Advances in the Synthesis of Indoles with Partially Hydrogenated Benzene Ring (Tetrahydroindoles)

Synthesis of 3-substituted tetrahydroindol-4-one

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