New applications of pyridinium ylides toward heterocyclic synthesis

LD Funt, MS Novikov, AF Khlebnikov - Tetrahedron, 2020 - Elsevier
The recent advances in the syntheses of various heterocycles based on pyridinium ylides
are described. Depending on the reactivity of the pyridinium ylides and the reactants, a …

Indolizine Synthesis through Annulation of Pyridinium 1, 4‐Thiolates and Copper Carbenes: A Predictive Catalysis Approach

R Monreal‐Corona, À Díaz‐Jiménez… - Advanced Synthesis …, 2023 - Wiley Online Library
Predictive catalysis was applied to the reaction of pyridinium 1, 4‐zwitterionic thiolates with a
copper carbene. Theoretical calculations were first performed to determine the suitability of …

Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines through Decarboxylative/Dehydrofluorinative [3 + 2] Cycloaddition Aromatization of Isoquinolinium N-Ylides with …

W Xi, Y Zhang, H Wu, J Li, Y Wang, J Yang… - Organic …, 2023 - ACS Publications
A decarboxylative/dehydrofluorinative formal [3+ 2] cycloaddition aromatization of
isoquinolinium N-ylides with difluoroenoxysilanes has been developed. This methodology …

Synthesis of indolizines from pyridinium salts and ethyl bromodifluoroacetate

X Hou, S Zhou, Y Li, M Guo, W Zhao, X Tang… - Organic …, 2020 - ACS Publications
Here we present a novel annulation of pyridinium salts with BrCF2CO2Et to access the
indolizine derivatives with high efficiency. The α substitution of pyridine plays a key role in …

Regioselective [3+ 2] cycloaddition of di/trifluoromethylated hydrazonoyl chlorides with fluorinated nitroalkenes: a facile access to 3-di/trifluoroalkyl-5-fluoropyrazoles

N Zhang, H Ma, CW Cheung, FG Zhang… - Organic & …, 2023 - pubs.rsc.org
Herein we describe the base-mediated [3+ 2] cycloaddition reaction of di/trifluoromethylated
hydrazonoyl chlorides with fluorinated nitroalkenes. The reaction protocol provides a direct …

Indolizines and their hetero/benzo derivatives in reactions of [8+ 2] cycloaddition

EV Babaev, IA Shadrin - Molecules, 2021 - mdpi.com
Peculiarities of [8+ 2] cycloaddition of acetylenes to indolizines are reviewed. Especially
mentioned are indolizines with leaving groups at positions 3 and 5. Cycloaddition to aza …

Copper-mediated oxidative [3+ 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro-and 3-nitro-pyrazolo [1, 5-a] pyridines

VA Motornov, AA Tabolin, YV Nelyubina… - Organic & …, 2020 - pubs.rsc.org
An efficient route to pyrazolo [1, 5-a] pyridines by Cu (OAc) 2-promoted oxidative [3+ 2]-
annulation of nitroalkenes with in situ generated pyridinium imines is developed. The …

[3 + 2]-Annulation of gem-Difluoroalkenes and Pyridinium Ylides: Access to Functionalized 2-Fluoroindolizines

JQ Zhang, D Hu, J Song, H Ren - The Journal of Organic …, 2021 - ACS Publications
A [3+ 2]-annulation of gem-difluoroalkenes and pyridinium ylides was developed employing
ambient air as the sole oxidant in an open-vessel manner, affording a series of …

[3+ 2] cycloaddition for the assembly of indolizine-based heterocyclic sulfonyl fluorides

H Xiong, J Wu, HL Qin - Organic Chemistry Frontiers, 2023 - pubs.rsc.org
Presented herein is a method for the construction of indolizine-based heterocyclic sulfonyl
fluorides through [3+ 2] cycloaddition of isoquinolinium/quinolinium salts and 1 …

Regioselective synthesis of 4-fluoro-1, 5-disubstituted-1, 2, 3-triazoles from synthetic surrogates of α-fluoroalkynes

S Jana, S Adhikari, MR Cox, S Roy - Chemical Communications, 2020 - pubs.rsc.org
α-Fluoroalkynes are elusive molecules due to their instability and inaccessibility. Here, we
show that α-fluoronitroalkenes can serve as synthetic surrogates of α-fluoroalkynes in [3+ 2] …