The Chemistry of the Pyrrocolines and the Octahydropyrrocolines.

Borrows, E. T.; Holland, D. O.

doi:10.1021/cr60133a005

Cited by 42 publications

(12 citation statements)

References 43 publications

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“…Indolizine (1) is one of the fundamental nitrogen heterocyclic systems which has been neglected in comparison to its isomer indole (1). Recently interest has been generated in this system since Boekelheide and co-workers have shown indolizine adds to activated acetylenes under dehydrogenating conditions to form the theoretically important class of cyclazines (2) in a reaction in which the indolizine reacts as an azomethine ylide, 1,3-dipole (3).…”

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confidence: 99%

Reaction of Cyclopropenones with Heteroaromatic Nitrogen Compounds

Lown¹,

Matsumoto²

1971

Can. J. Chem.

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Diphenylcyclopropenone reacts with a variety of heteroaromatic nitrogen compounds to give in good yield either (a) 1,2-diphenyl-3-indolizinyl cis-1,2-diphenyl acrylates and aza analogs, (b) 5,6-diphenyl-7-hydroxypyrrolo[l,2-blpyridazines and similar structures, or (c) adducts in which cycloaddition takes place to an N=N bond. Proof of structure of the new heterocycles is based on deuterium labelling experiments, hydrogenolysis to known compounds, and the preparation of chloro and iminoether derivatives. Cycloheptenocyclopropenones in the examples studied form heterocycles of type b.La diphtnylcyclopropknone rtagit avec une varittt de composes htttroaromatiques contenant de I'azote et conduit avec de bons rendements soit (a) aux cis-diphtnyl-1,2 acrylates (et leurs analogues azotes) de diphknyl-1,2 indolizinyle-3, (b) aux diphknyl-5,6 hydroxy-7 pyrrolo[l,2-blpyridazines et structures similaires, ou (c) des composes d'addition dans lesquels la cycloaddition se fait sur le lien -N=N-.Les preuves de structure de ces composts sont bastes sur des experiences impliquant des marquages par le deuttrium, des hydrogtnolyses conduisant a des composes connus et la preparation de dtrivts chlorts et iminoethers. Dans les cas examints, les cyclohepttnocycloproptnones conduisent des htttrocycles du type b.

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confidence: 99%

Reaction of Cyclopropenones with Heteroaromatic Nitrogen Compounds

Lown¹,

Matsumoto²

1971

Can. J. Chem.

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“…Despite this limitation, the method remains one of the most efficient syntheses of indolizines [28–31] owing to the simple working procedure and the large number of 2-substituted pyridines that are commercially available. An overview of Chichibabin indolizine syntheses has been included in the reviews dedicated to indolizine syntheses and their applications in medicine and advanced materials [6–15]. …”

Section: Resultsmentioning

confidence: 99%

“…As a result, it was of interest to prepare analogous compounds containing a pyrroloazine directly attached to the C-4 position of a sydnone ring. From a survey of the literature data [6–15] and based on our previous findings [16–19] it was concluded that the heterocycle in the pyrroloazine series most suitable for this study would be indolizine ( 2 ).…”

Section: Introductionmentioning

confidence: 99%

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Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

Albota

Caira

Drăghici

et al. 2016

Beilstein J. Org. Chem.

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The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of the new compounds were assigned by FTIR, NMR spectroscopy and X-ray analysis.

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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). Indolizines (indolizine derivatives) are heterocyclic compounds comprised of indolizine heterocyclic nuclei.…”

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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The Chemistry of the Pyrrocolines and the Octahydropyrrocolines.

Cited by 42 publications

References 43 publications

Reaction of Cyclopropenones with Heteroaromatic Nitrogen Compounds

Reaction of Cyclopropenones with Heteroaromatic Nitrogen Compounds

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

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

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