Denitrogenative transformations of aryl-fused 1,2,3-triazoles

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

Comprehensive Summary Indolizine is a nitrogen‐containing heterocycle with strong aromaticity, possessing delocalized 10π‐electron system. Based on the indolizine scaffolds, numerous molecules biological activity and organic functional materials have been synthesized. Since 2016, over 110 papers published synthesis of but reviews synthesizing scaffolds incomplete not up‐to‐date. Herein, from perspective structure combination pyrrole pyridine ring, we focus construction through diversity starting substrates, including derivatives (N1‐substituted pyridinium salt derivatives, C2‐substituted N1‐ C2‐free substituted derivatives), unoriginal ring substrates. Furthermore, corresponding reaction mechanisms synthetic methodologies are also elaborated. Therefore, this review only paves way for provides insight into exploring new modes constructing heterocycles. Key Scientists was discovered by Angeli in 1890 first prepared Scholtz 1912 α‐picoline acetic anhydride. A general approach developed Chichibabin 1927, that practical value preparation 2‐alkyl‐ or 2‐arylindolizines. The closure quaternary halides. At begining 21st century, Basavaiah introduced dimension Baylis‐Hillman chemistry leading to novel facile convenient methodology one‐pot operation. In 2010, Barluenga reported Cu(I)‐catalyzed regioselective [3+2] cyclization unsubstituted pyridines toward alkenyldiazoacetates functionalized successful example metal‐catalyzed π‐deficient heterocyclic system alkenyldiazo compounds. 2019 2022, Xi Liu exploited methods non‐pyridine as synthesize indolizines, respectively. Guo an environmentally benign electrooxidative formyl‐ acyl‐substituted indolizines.

Language: Английский

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Rhodium-Catalyzed 3-Aza-Cope Rearrangement of Protic N-Allyl Enammonium Ylides Enabled by Resonance Assisted H-Bonding

Published: July 31, 2024

Herein, we present the design of a new class Rh-bound protic N-allyl enammonium ylides and its stereoselective 3-aza-Cope rearrangement. These transient are generated in situ by Rh-catalyzed reaction vinyldiazo com-pounds N-secondary-(Z)--enamino carbonyl compounds, under mild conditions. Mechanistic studies revealed that resonance-assisted hydrogen bonding (RAHB) ylide promotes exclusively [3,3] rear-rangement disfavouring both 1,2-proton transfer (NH-insertion) direct carbenoid C-C bond formation. This was used synthesis multi-substituted pyrroles, dihydropyrroles, deuterated tetrahy-droindoles, pyrroloindole scaffold an antitumor UV-protecting agent terreusinone.

Language: Английский

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Regiospecific Synthesis of 1,4-Diaryl-5-cyano-1,2,3-triazoles and Their Photoconversion to 2- or 3-Cyanoindoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12610 - 12618

Published: Aug. 28, 2024

We report the synthesis of 1,4-diaryl-5-cyano-1,2,3-triazoles from azides and alkynes via two copper-mediated steps. Aryl-substituted cyanotriazoles are emissive in nonpolar solvents. When

Language: Английский

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