Divergent Synthesis of F- and CF₃-Containing N-Fused Heterocycles Enabled by Fragmentation Cycloaddition of β-CF₃-1,3-Enynes with N-Aminopyridiniums Ylides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1255 - 1260

Published: Feb. 7, 2024

The two novel cyclization modes of β-CF

Language: Английский

---

Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5717 - 5734

Published: Jan. 1, 2023

Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide summary the advancements achieved metal-catalyzed functionalization using VC.

Language: Английский

---

One-step synthesis of cyanated pyrazolo[1,5-a]pyridines utilizing N-aminopyridines as a 1,3-dipole and a nitrogen source

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 2892 - 2897

Published: Jan. 1, 2023

By utilizing the dual reactivity function of N -aminopyridinium ylides, we developed a direct [3 + 2]-cycloaddition ylides and ynals to build pyrazolo[1,5- ]pyridine core while introducing cyano group.

Language: Английский

---

Transition metal-free annulative vinylene transfer via the 1,3-dipolar reaction of N-ylides: access to benzo-fused indolizines

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(48), P. 9604 - 9608

Published: Jan. 1, 2022

An efficient metal-free annulative vinylene transfer protocol for the synthesis of benzo-fused indolizines via 1,3-dipolar cycloadditions N-ylides with carbonate has been developed. Vinylene serves as an acetylene surrogate without any external oxidant involved. This transformation leads to direct construction versatile indolizine derivatives in moderate good yields.

Language: Английский

---

Copper-Catalyzed Formal [4 + 1] Annulation toward Diverse Trifunctionalized Indolizines from Pyridinium 1,4-Zwitterionic Thiolates and Diazos

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7199 - 7207

Published: May 12, 2023

Pyridinium 1,4-zwitterionic thiolates were regarded as powerful and versatile building blocks to prepare nitrogen- sulfur-containing heterocycles. Herein, we reported a copper-catalyzed formal [4 + 1] annulation of pyridinium diazo compounds without any additives access library trifunctionalized indolizines in good yields. Besides, isoquinolinium imidazolium also applied this reaction. Of particular note is that various functional groups such -CO2R, -CO2NR2, -CF3, -CN, -(O)P(OR)2 could be easily introduced into cycloaddition products by strategy.

Language: Английский

---

Vinylene Carbonate as Synthon in Transition Metal‐Catalyzed C−H Bond Activation/Annulation Reactions

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3400 - 3412

Published: Sept. 6, 2023

Abstract Recently, vinylene carbonate has been developed as a powerful synthon in transition metal‐catalyzed C−H bond activation/cyclization reactions. This review introduces recent progress the use of reactant, by analyzing and comparing reaction models involving surrogate ethynol, acetylene, acetylation reagents or other reactants, while addressing related mechanisms synthetic applications.

Language: Английский

---

DBU‐Promoted [3 + 2] Cyclization/Retro‐Mannich Cascade Reaction of N‐Aminoisoquinolinium and N‐Aminoquinolinium Derivatives with para‐Quinone Methides

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

---

Five-Component [2 + 2 + 1 + 1] Tandem Benzannulation Leading to Multifunctionalized Aromatic Amines

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

---

[3 + 2] Cycloaddition of N-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-a]quinoline and Pyrazolo[5,1-a]isoquinoline Derivatives

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 16, 2025

In this study, we reported the utilization of vinylsulfonium salt as a highly efficient dipolarophile, leveraging facile leaving ability its sulfide moiety, to engage in [3 + 2] cycloaddition with N-amino(iso)quinolinium salts. This approach facilitates construction various C1/C2-unsubstituted pyrazolo(iso)quinoline skeletons. The transformation is conducted under catalyst- and external oxidant-free conditions. Furthermore, extended gram-scale reaction demonstrates practical applicability developed protocol.

Language: Английский

---

Bisphosphonium salt catalyzed [3 + 2] annulation of N-tosylimino(iso)quinolinium ylides with aryl olefins under blue LED irradiation

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3827 - 3832

Published: Jan. 1, 2024

A visible-light-induced [3 + 2] annulation of N -tosylimino(iso)quinolinium ylides with aryl olefins, catalyzed by a bisphosphonium salt has been developed. Furthermore, the synthesis method salts was improved.

Language: Английский

---