Metal-free synthesis of carbamoylated dihydroquinolinones via cascade radical annulation of cinnamamides with oxamic acids

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1821 - 1833

Published: Jan. 1, 2024

Metal-free synthesis of medicinally important carbamoylated dihydroquinolinones using readily available, cheap and environment-friendly materials with good to excellent yields.

Language: Английский

---

Base-Promoted [4 + 1 + 1] Multicomponent Tandem Cycloaddition of Ortho-Substituted Nitroarenes, Aldehydes, and Ammonium Salts To Access 2,4-Substituted Quinazoline Frameworks

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(5), P. 1982 - 1995

Published: Jan. 23, 2025

We report a base-promoted, metal-free multicomponent tandem reaction, involving [4 + 1 1] cycloaddition process between ortho-substituted nitroarenes, aldehydes, and ammonium salts. Modifying the substituents on nitroaromatic compounds effectively provides structurally diverse 2-substituted 4-alkenylquinazolines with good to excellent yields (77%-90% quinazoline 51 examples) high tolerance for various inorganic salts (13 examples, such as NH3·H2O, NH4Cl, NH4HF2). A new method constructing 2,4-substituted selectivity from simple nitrogen source was developed, reaction can be scaled up gram scale. Additionally, this also facilitates preparation of organic molecules photophysical properties, offering insights into further transformation quinazolines.

Language: Английский

---

Visible-light-induced three-component reactions of α-diazoesters, quinazolinones and cyclic ethers toward quinazoline-based hybrids

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(21), P. 4332 - 4346

Published: Jan. 1, 2024

Visible-light-induced three-component reactions, which were performed under extremely mild conditions without the need for any additional additives and catalysts showed a broad substrate scope, gave corresponding quinazoline-based hybrids in good to excellent yields.

Language: Английский

---

Metal‐Free Regioselective Direct C(4)−H Amination of Quinazoline with N‐fluorobenzenesulfonimide

ChemPlusChem, Journal Year: 2024, Volume and Issue: 89(11)

Published: July 18, 2024

Abstract A facile C−H amination of quinazoline employing N ‐fluorobenzenesulfonimide (NFSI) as the source has been disclosed in absence any metal, oxidant or additive. The methodology shows a board range quinazolines with different functional groups moderate to good yields up 87 %. Furthermore, gram‐scale reaction, desulfonylation amine and synthesis pharmaceutical intermediate were also investigated, which demonstrates potential applications medicinal chemistry. plausible mechanism is proposed via F + transfer accompanied by removal one molecule PhSO 2 F. DFT studies experimental work suggest that more favorable than free radical one.

Language: Английский

---

Metal-free, direct acylation of purines to access C⁶-acylated purine derivatives induced by TBHP via Minisci-type reaction

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(12), P. 5167 - 5172

Published: Jan. 1, 2024

The highly C 6 -regioselective acylation of purines with aldehydes was developed to access -acylated via green radical reactions without metal catalysts or light.

Language: Английский

---

Ag-Catalyzed Cross-Dehydrogenative-Coupling for the Synthesis of 1,4-Dioxan-2yl Substituted Qunazoline Hybrids in Aqueous Media

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(37), P. 7725 - 7735

Published: Jan. 1, 2024

We herein developed an effective approach for the construction of 2- or 4-(1,4-dioxan-2-yl) substituted quinazolines under mild conditions. A silver-K

Language: Английский

---

Six-membered ring systems: Diazines and benzo derivatives

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 355 - 393

Published: Jan. 1, 2024

---

Electrochemical Synthesis of Quinazolines: N–H/C(sp³)–H Coupling of o-Carbonyl Anilines with Amino Acids and Amines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

A mild and efficient electrochemical protocol for the synthesis of quinazolines through N-H/C(sp

Language: Английский

---