Site-Selective Copper–N-Heterocyclic Carbene-Catalyzed C(sp2)–C(sp) Cross-Coupling of Aryl Thianthrenium Salts DOI
Jin Zhang, Hangsheng Yang, Li Sun

et al.

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

Published: March 23, 2025

This work demonstrates Cu–NHC (NHC = N-heterocyclic carbene) catalyzed alkynylation of aryl thianthrenium salts via thiazol-2-ylidene ligands, achieving a Pd-free Sonogashira coupling with broad substrate compatibility and functional group tolerance. Late-stage pharmaceutical rare alkynylative C–H functionalization/ring-opening pathways are enabled. Thiazol-2-ylidenes, featuring "half-umbrella"-shaped geometry, exhibit superior catalytic performance over traditional imidazol-2-ylidenes, underscoring their unique ligand efficacy. catalysis enables the use as versatile electrophiles for diverse cross-couplings under mild conditions.

Language: Английский

Fe3O4@Sap/Cu(ii): an efficient magnetically recoverable green nanocatalyst for the preparation of acridine and quinazoline derivatives in aqueous media at room temperature DOI Creative Commons
Milad Kazemnejadi, Mohammad Ali Nasseri, Safoora Sheikh

et al.

RSC Advances, Journal Year: 2021, Volume and Issue: 11(26), P. 15989 - 16003

Published: Jan. 1, 2021

A highly efficient, robust, and green protocol has been developed for the synthesis of acridine quinazoline derivatives in water under mild reaction conditions using a Fe3O4@Sap/Cu(ii) nanocomposite as an efficient heterogeneous catalyst.

Language: Английский

Citations

22

Cobalt-Catalyzed Isocyanide-Based Three-Component Cascade for the Synthesis of Quinazolines DOI
Shuai Jiang, Wenbin Cao, Xiaoping Xu

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(17), P. 6740 - 6744

Published: Aug. 12, 2021

A Co-catalyzed cyclization reaction of isocyanides, azides, and amines to access quinazoline derivatives was described. This protocol features a high atom economy, mild conditions, excellent yields, broad substrate scope. cascade involved three or four C–N bonds the formation one two rings. The quinazolin-4(H)-imines obtained are proven be versatile intermediates for further valuable transformations. It also found that cobalt catalyst could isolated from mixture reused.

Language: Английский

Citations

21

[CMMIM][BF4] Ionic Liquid-Catalyzed Facile, One-Pot Synthesis of Chromeno[4,3-d]pyrido[1,2-a]pyrimidin-6-ones: Evaluation of Their Photophysical Properties and Theoretical Calculations DOI Creative Commons
Sai Deepak Pasuparthy, Barnali Maiti

ACS Omega, Journal Year: 2022, Volume and Issue: 7(43), P. 39147 - 39158

Published: Oct. 17, 2022

Herein, we have developed a novel synthetic route for the synthesis of chromeno[4,3-d]pyrido[1,2-a]pyrimidin-6-one derivatives 8a-q using an acid ionic liquid [CMMIM][BF4-] 4 via one-pot, three-component in aqueous ethanol at room temperature. A series 17 been successfully prepared with up to 93% yield. All synthesized were well characterized 1H-NMR, 13C-NMR, and FT-IR spectral techniques. Additionally, photophysical properties 12 selected including molar extinction coefficient (ε), Stokes shift (Δυ̅), quantum yield (Φ) varying from 0.52095 × 104 0.93248 104, 4216 4668 cm-1, 0.0088 0.0459, respectively, determined. Furthermore, experimental data are supported by density functional theory (DFT) time-dependent DFT calculations. Theoretical investigations showed trend similar results.

Language: Английский

Citations

16

Ru(II)‐Catalyzed Selective C—H Alkynylation of Isoquinolones, Quinazolones and Phthalazinones with Bromoalkynes DOI

Quanjian Luo,

Han‐Chi Wang,

Jing Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1686 - 1690

Published: March 15, 2024

Comprehensive Summary A new, selective Ru(II)‐catalyzed alkynylation reaction of isoquinolones, quinazolones and phthalazinones with readily available bromoalkynes has been developed. This enables the construction a new C(sp 2 )‐C(sp) bond through C—H activation C—Br functionalization, offers an effective route to synthesizing highly valuable alkynylated isoquinolone, quinazolone phthalazinone derivatives wide substrate scope high selectivity.

Language: Английский

Citations

3

Site-Selective Copper–N-Heterocyclic Carbene-Catalyzed C(sp2)–C(sp) Cross-Coupling of Aryl Thianthrenium Salts DOI
Jin Zhang, Hangsheng Yang, Li Sun

et al.

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

Published: March 23, 2025

This work demonstrates Cu–NHC (NHC = N-heterocyclic carbene) catalyzed alkynylation of aryl thianthrenium salts via thiazol-2-ylidene ligands, achieving a Pd-free Sonogashira coupling with broad substrate compatibility and functional group tolerance. Late-stage pharmaceutical rare alkynylative C–H functionalization/ring-opening pathways are enabled. Thiazol-2-ylidenes, featuring "half-umbrella"-shaped geometry, exhibit superior catalytic performance over traditional imidazol-2-ylidenes, underscoring their unique ligand efficacy. catalysis enables the use as versatile electrophiles for diverse cross-couplings under mild conditions.

Language: Английский

Citations

0