Tandem Michael addition/elimination – novel reactivity of pyridinium ylides in reaction with electron-deficient alkenes

Izmest’ev, Alexei N.; Motornov, Vladimir; Vinogradov, Dmitry B.; Ioffe, Sema L.; Кравченко, Ангелина Н.; Газиева, Галина А.

doi:10.1039/d2qo00911k

Cited by 6 publications

(3 citation statements)

References 37 publications

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“…The developed method is also applicable to substrates 8a – c [ 23 ] substituted in the methylidene fragment. Thus, compounds 8a – c were converted into the corresponding potassium salts 3k – m under the same conditions (MeOH, room temperature, 1–24 h) ( Scheme 7 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

Vinogradov

Izmest’ev

Кравченко

et al. 2023

Beilstein J. Org. Chem.

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A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine.

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Section: Resultsmentioning

confidence: 99%

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

Vinogradov

Izmest’ev

Кравченко

et al. 2023

Beilstein J. Org. Chem.

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“…The authors have cited additional references within the Supporting Information. [21][22][23][24][25][26][27][28][29][30][31][32][33] The Supporting Information includes Studies of reaction conditions, general procedure, and characterization data of the products.…”

Section: Supporting Information Summarymentioning

confidence: 99%

Aerobic Synthesis and Nucleophilicity of 2,3‐Dihydroindolizines

Qiu,

2023

ChemistrySelect

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Herein, we reported a practical and metal‐free synthesis of 2,3‐dihydroindolizines using N‐alkyl pyridinium salts and electron‐deficient alkenes with ambient air as a sole oxidant. Interestingly, a halogen bond donor (penta‐fluoroiodobenzene 20 mol %) was successfully applied to promote this partial oxidation by slowing down the undesired decomposition processes, probably because of the formation of a halogen‐bonded adduct. Moreover, the C1 position of 2,3‐dihydroindolizines was utilized as a good nucleophile for nucleophilic aromatic substitution with 4‐iodo‐1‐methylpyridin‐1‐ium trifluoromethanesulfonate as electrophile and provided a new‐type dipyridinium compound effectively.

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“…In recent years, some new synthetic methods have been developed for the construction of substituted pyridine, pyrrole, and indolizine rings, etc. via ring-transformation strategies from cheap and easily available pyridinium salts . We previously reported a new synthetic approach for pyrrole-2-carbaldehydes from pyridinium salts via a ring-opening/reclosing process .…”

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confidence: 99%

Tandem Ring-Contraction/Regioselective C–H Iodination Reaction of Pyridinium Salts

Tang

Zhao

et al. 2023

J. Org. Chem.

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A facile route for direct access to the 4-iodopyrrole-2-carbaldehydes from pyridinium salts has been successfully developed, which undergoes cascade pyrrole-2-carbaldehydes construction/selective C4 position iodination process. Using Na 2 S 2 O 8 as an oxidant and readily available sodium iodide as an iodine source, a variety of 4-iodopyrrole-2-carbaldehydes were obtained in good to excellent yields. Atom-and stepeconomy, good functional group tolerance, high regioselectivity, as well as mild conditions entail this transformation an alternative strategy for enriching pyrroles library.

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Tandem Michael addition/elimination – novel reactivity of pyridinium ylides in reaction with electron-deficient alkenes

Abstract: Novel reactivity of pyridinium ylides in reaction with annulated 4-oxothiazolidin-5-ylidenes as electron-deficient alkenes involving a cascade Michael addition/elimination process is described. The method provides a broad variety of functionalized products...

Cited by 6 publications

References 37 publications

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

Aerobic Synthesis and Nucleophilicity of 2,3‐Dihydroindolizines

Tandem Ring-Contraction/Regioselective C–H Iodination Reaction of Pyridinium Salts

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