[(5 + 1) ‐ 1] Cyclization of Nitroepoxides to Pyridinium 1,4‐Zwitterionic Thiolates for the Synthesis of Indolizine Derivatives DOI

Alhajaj Almaani,

Ahmad Takallou, Yazdanbakhsh Lotfi Nosood

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract The synthesis of indolizine derivatives was achieved through the reaction pyridinium 1,4‐zwitterionic thiolates with a diverse array 2‐methyl‐2‐nitro‐3‐aryloxiranes. Subsequent investigations unveiled synthetic route to indolizines via stepwise [(5+1)−1] pathway, unstable pyridothiazines serving as transient intermediates. DFT calculations elucidated that this transformation entails sequential annulation, deacylation, desulfurization, and oxidation steps.

Language: Английский

Construction of 3,6-Difluoropyridones via a Double Defluorinative [3 + 3] Annulation of α-Fluoro-α-sulfonylacetamides with 2-CF3-Alkenes DOI

Sanoop P. Chandrasekharan,

Usha Yadav, Kishor Mohanan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 8, 2025

A remarkably simple and efficient double defluorinative [3 + 3] annulation approach involving N-phenyl-α-fluoro-α-phenylsulfonylacetamide 2-CF3-alkenes to access N-phenyl-3,6-difluoropyridone derivatives has been achieved. The key the success of this single-step synthesis difluoropyridones is strategic utilization for consecutive allylic vinylic substitution reactions a desulfonylation cascade. We could also show that these serve as versatile platform C-6-selective functionalizations.

Language: Английский

Citations

0

Metal-free catalytic de novo construction of multi-functionalized trifluoromethylarenes through [3 + 3] benzannulation at low catalyst loadings DOI

Qing He,

Yuanyuan Xiang, Rui Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A low catalyst loading and transition metal-free benzannulation of β,γ-alkynyl-α-keto esters CF 3 -alkenes has been developed through Michael-triggered [3 + 3] annulation.

Language: Английский

Citations

0

Highly regio- and stereo-controlled synthesis of (Z)-4-(trifluoromethyl)-3-(phenylthio)-1-substituted-but-3-en-1-ynes via hydroalkynylation of alkynyl thioethers DOI

Akihiro Koga,

Takeshi Hanamoto

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We carried out the first reaction of palladium-catalyzed hydroalkynylation alkynylthioethers with terminal acetylenes.

Language: Английский

Citations

0

Silver-Catalyzed Cascade Approach to Access Fused Pyrazolo-naphthyridine and -isoquinoline Backbones and Investigation of Their Photophysical Properties DOI Creative Commons

Fatemeh Abdiyan Mobarakeh,

Mohammad Rezaei-Gohar,

Kamran Amiri

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: unknown

Published: April 4, 2025

We describe a novel approach for synthesizing diverse fused heterocyclic compounds by utilizing sequential silver(I) catalyzed reaction between readily obtainable N-amidonaphthyridin ylide and dialkyl acetylenedicarboxylates. This method provides an efficient the selective synthesis of tetracyclic ring-fused 1,6-naphthyridine isoquinoline derivatives, offering exceptional structural diversity. In addition, title constitute interesting class luminophores with tunable emission solvatochromicity.

Language: Английский

Citations

0

DBU‐Promoted [3 + 2] Cyclization/Retro‐Mannich Cascade Reaction of N‐Aminoisoquinolinium and N‐Aminoquinolinium Derivatives with para‐Quinone Methides DOI
Shaohong Ma, Mingyang Chen, Zifeng Yang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2003 - 2007

Published: March 12, 2024

Abstract A DBU‐promoted [3+2] cyclization/retro‐Mannich cascade reaction of N ‐aminoisoquinolinium and ‐aminoquinolinium derivatives with para ‐quinone methides has been established, employing a C=C double bond cleavage. broad range salts, are well tolerated, providing the corresponding rearrangement products. Moreover, scaled‐up reactions diverse derivatizations products were also investigated discussed.

Language: Английский

Citations

3

Trifluoromethyl Group (CF3) Induced Regioselective Larock Indole Synthesis from Unsymmetric β-CF3-1,3-enynes DOI

Yan‐Hua Qiu,

Peng-Xiang Ma,

Wen‐Hao Shao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

The indole skeleton exists widely in natural products, pharmaceuticals, and materials. We disclose here a trifluoromethyl group induced regioselective Larock synthetic method from unsymmetric 2-CF3-1,3-enynes. presence of is determinable for the regioselectivity. Once CF3 was replaced with methyl or phenyl group, ratio 1:1 to 1:1.4 isomers were obtained. This strategy features good regioselectivity, broad substrate scope, high functional tolerance. protocol reported offers an alternative solution rare 3,4-functionalization products further transformed show distinctive reactivity hydroboration–oxidation hydro-bromination.

Language: Английский

Citations

0

Five-Component [2 + 2 + 1 + 1] Tandem Benzannulation Leading to Multifunctionalized Aromatic Amines DOI
Hexiang Wang,

Shuting Li,

Xiaoying Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9648 - 9653

Published: Nov. 1, 2024

An unprecedented five-component [2 + 2 1 1] benzannulation strategy for regioselective assembly of densely functionalized aromatic amines from two ynals, malononitriles, and sodium sulfinates is established. The protocol enables the efficient installation five substituents on a benzene ring via formation multiple chemical bonds in single operation, providing various multifunctionalized primary moderate to good yields. Additionally, three-component [3 cycloaddition NH4SCN was also achieved produce 2-amnopyridine derivatives with serving as an ammonia surrogate.

Language: Английский

Citations

3

Recent Advances on Direct Phosphorothiolation Reactions DOI

Haifa Zheng,

Ju Peng,

Xiang Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: July 23, 2024

Abstract Organophosphorothioates are organic molecules containing sulfur and phosphorus, with significant biological activity physicochemical properties, widely used in synthesis, medicinal chemistry, the agrochemical industry. In particular, many phosphorothioates display a variety of activities, such as antifungal, antibacterial, anti‐parasite, anticancer, so on. Traditionally, synthesis has mainly relied on indirect methods involving construction S−P bond. recent years, direct phosphorothiolation gained attention reliable rapid method for introducing −S−P(O)(OR) 2 group into parent molecules. This article reviews latest advances reactions, categorized based different sources group.

Language: Английский

Citations

2

Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans DOI
Chun‐Yan Wu, Xiang‐Long Chen, Dongsheng Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4

Language: Английский

Citations

2

Recent Advances in Photoinduced Borylation via N-Heterocyclic Carbene Boryl Radicals DOI
Xiang Liu, Chen Xu,

Xuesi Zhou

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 28, 2024

Abstract Organoboron compounds are recognized as essential synthetic intermediates in organic chemistry and have found broad applications pharmaceutical materials science. In recent years, the development of novel boronating reagents has opened new avenues for synthesis organoboron compounds. Among these, N-heterocyclic carbene boranes (NHC-boranes), with their unique advantages, garnered sustained interest evolved into important precursors boron-centered radicals, participating a diverse array visible-light-induced borylation reactions. This short review primarily focuses on radical reactions involving NHC-boranes, summarizing latest advancements field offering inspiration subsequent research. 1 Introduction 2 Photoinduced Borylation via NHC-Boryl Radicals 2.1 Polyfluoroarenes 2.2 Arenes 2.3 Alkenes 2.4 Alkynes 2.5 Other Substrates 3 Conclusion Future Prospects

Language: Английский

Citations

1