A Novel Approach for the Synthesis of 5‐Pyridylindolizine Derivatives <i>via</i> 2‐(2‐Pyridyl)pyridinium Ylides

Georgescu, Emilian; Dumitraşcu, Florea; Georgescu, Florentina; Drăghici, Constantin; Barbu, Loredana

doi:10.1002/jhet.997

Cited by 10 publications

(6 citation statements)

References 28 publications

(36 reference statements)

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“…[27][28][29][30] Usually, this multistep process starts with the preparation of N-heterocyclic quaternary salts with -halo carbonyl compounds, in situ conversion into corresponding heterocyclic N-ylides in the presence of an inorganic or organic base and 3+2 dipolar cycloaddition reactions of heterocyclic N-ylides with electron-deficient alkynes or alkenes. [31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] Our group has developed a simple one-pot, multicomponent synthetic strategy towards N-bridgehead heterocyclic compounds based on the consecutive quaternization of the N-heteroaromatic compound, in situ generation of the heterocyclic N-ylide, 3+2 dipolar cycloaddition reaction to an electron-deficient alkyne and aromatization sequence, using an epoxide as solvent and acid scavenger. [46][47][48][49][50][51][52][53][54][55] A range of new indolizines and azaindolizines were synthesized via 3+2 dipolar cycloaddition reactions of cycloimmonium ylides, generated from the various N-heterocycles such as pyridine, quinoline, isoquinoline, pyridazine, pyrimidine, phthalazine and benzimidazole derivatives with diverse phenacyl bromides, alkyl bromoacetates, 3-(2-bromoacetyl)-2H-chromen-2-one and electrondeficient alkynes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and spectroscopic properties of novel indolizines and azaindolizines

NICOLESCU,

AIRINEI,

GEORGESCU

et al. 2023

Rev.Roum.Chim.

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Novel indolizines and pyrrolo[1,2-c]pyrimidines bearing a 3-carbonylchromen-2-one moiety on the pyrrole rings were synthesized and spectroscopic properties of some of synthesized compounds were investigated. Synthetic procedures started from 4-substituted pyrimidines, 3-(2-bromoacetyl)-2H-chromen-2-one and electron-deficient alkynes via 3+2 dipolar cycloaddition of cycloimmonium-ylides, generated in situ from their corresponding quaternary salts, in the presence of an epoxide playing the role of acid scavenger and reaction solvent. The structures of novel compounds were confirmed by chemical analyses, IR and NMR spectroscopy. Spectroscopic properties of some of the synthesized compounds were investigated.

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Section: Introductionmentioning

confidence: 99%

Synthesis and spectroscopic properties of novel indolizines and azaindolizines

NICOLESCU,

AIRINEI,

GEORGESCU

et al. 2023

Rev.Roum.Chim.

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“…Indolizine is a heteroaromatic molecule composed of two condensed rings (five and six members) and a bridging nitrogen atom (1). Indolizine has been referred to by various names in the literature, including pyrindole, pyrrodine, pyrrolo [1,2-a]pyridine, and pyrrocoline (2).…”

Section: Introductionmentioning

confidence: 99%

QSER modeling of half-wave oxidation potential of indolizines by theoretical descriptors

Bouarra

Nadji

Kherouf

et al. 2022

Journal of the Turkish Chemical Society Section A: Chemistry

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Indolizine derivatives hold essential biological functions and have been researched for hypoglycemic, antibacterial, anti-inflammatory, analgesic, and anti-tumor actions. Indolizine scaffold has intrigued conjecture and continuous attention and has become an effective parent system for generating powerful novel medication candidates. This research focused on applying the quantitative structure-electrochemistry relationship (QSER) approach to the half-wave potential (E1/2) for Indolizine derivatives using theoretical molecular descriptors. After calculating the descriptors and splitting the data into both sets, training and prediction. The QSER model was constructed using the Genetic Algorithm/Multiple Linear Regression (GA/MLR) technique, which was used to choose the optimal descriptors for the model. A four-parameter model has been established. Many assessment procedures, including cross-validation, external validation, and Y-scrambling testing, were used to assess the model's performance. Furthermore, the applicability domain (AD) was investigated using the Williams and Insubria graphs to assess the correctness of the established model's predictions. The constructed model exhibits great goodness-of-fit to experimental data, as well as high stability (R²=0.893, Q²LOO= 0.851, Q²LMO=0.843 RMSEtr= 0.052, s= 0.056). Prediction results show a good agreement with the experimental data of E1/2 (R²ext= 0.912, Q²F1= 0.883, Q²F2= 0.883, Q²F3= 0.919, CCCext= 0.942, RMSEext=0.045).

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“…However, in some cases alternative routes could be useful to achieve structural variety [ 13 ]. An alternative route is to start from accessible simple heteroarenes linked by a single bond and to transform one of them or both into more complex structures [ 14 – 15 ].…”

Section: Introductionmentioning

confidence: 99%

“…For example, starting from bispyridyl derivatives such as 1 and 3 , fluorescent compounds from the class of indolizines, as for example compounds 2 , 4 and 5 ( Fig. 1 ) were obtained [ 14 – 15 ].…”

Section: Introductionmentioning

confidence: 99%

Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

Popa

Georgescu²,

Caira

et al. 2015

Beilstein J. Org. Chem.

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SummaryThe three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric hindrance directs the reaction to the pyrimidinium N-ylides and, subsequently, to the formation of the pyrrolo[1,2-c]pyrimidines. The new pyrrolo[1,2-c]pyrimidines and the new indolizines were structurally characterized through NMR spectroscopy. The X-ray structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported.

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A Novel Approach for the Synthesis of 5‐Pyridylindolizine Derivatives via 2‐(2‐Pyridyl)pyridinium Ylides

Cited by 10 publications

References 28 publications

Synthesis and spectroscopic properties of novel indolizines and azaindolizines

Synthesis and spectroscopic properties of novel indolizines and azaindolizines

QSER modeling of half-wave oxidation potential of indolizines by theoretical descriptors

Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

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