Radical-mediated photoredox hydroarylation with thiosulfonate

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2767 - 2770

Published: Jan. 1, 2023

Radical-mediated photoredox hydroarylation reaction of unactivated alkenes using thiosulfonate compounds as key radical precursors to synthesize pyridyquinazolinone and pyrroloquinazolinone derivatives is described.

Language: Английский

---

Metal-Free Photoinduced Hydrocyclization of Unactivated Alkenes toward Ring-Fused Quinazolin-4(3H)-ones via Intermolecular Hydrogen Atom Transfer

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1683 - 1688

Published: March 8, 2023

A visible-light-induced hydrocyclization of unactivated alkenes was developed using 3CzClIPN as the photocatalyst to generate substituted α-methyldeoxyvasicinones and α-methylmackinazolinones in moderate good yields. An intermolecular hydrogen atom transfer with THF source involved. Mechanism studies indicated that intramolecular addition situ formed aminal radical alkene generated polycyclic quinazolinone.

Language: Английский

---

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

---

Organic photoredox catalytic radical sulfonamidation/cyclization of unactivated alkenes towards polycyclic quinazolinones

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6290 - 6294

Published: Jan. 1, 2022

The synthesis of sulfonamidylated polycyclic quinazolinones was developed via visible-light-induced radical sulfonamidation/cyclization unactivated alkenes using 4CzIPN as the photocatalyst.

Language: Английский

---

Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

---

(NH₄)₂S₂O₈ promoted tandem radical cyclization of quinazolin-4(3H)-ones with oxamic acids for the construction of fused quinazolinones under metal-free conditions

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(11), P. 2241 - 2251

Published: Jan. 1, 2024

A novel cascade radical addition/cyclization reaction of non-activated olefins and oxamic acids has been proposed.

Language: Английский

---

Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(35), P. 4687 - 4690

Published: Jan. 1, 2024

A visible-light-induced carbophosphorylation/cyclization of N -homoallyl and -allyl aldehyde hydrazones with phosphine oxides was developed to obtain phosphorylated tetrahydropyridazines dihydropyrazoles.

Language: Английский

---

Photoinduced, Silver(I)-Mediated Synthesis of Ester-Substituted Fused Quinazolinones via Cascade Alkoxycarbonylation/Cyclization of Heterocycles Bearing Unactivated Alkenes

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5861 - 5874

Published: April 7, 2023

A new cascade alkoxycarbonylation/cyclization reaction of heterocycle-bearing unactivated alkenes is disclosed. The transformation mediated by silver carbonate under photoirradiation. This method provides efficient access to pharmaceutically valuable molecules and natural product analogues containing quinazolinone-fused esters. Furthermore, this protocol compatible with a variety quinazolinone-bearing alkyloxalyl chlorides that are readily prepared from abundant alcohols oxalyl chlorides.

Language: Английский

---

Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134497 - 134497

Published: Jan. 1, 2025

Language: Английский

---

Dicarbofunctionalization of unactivated alkenes via organo-photoredox catalysis in water: access to cyanoalkylated fused quinazolinones

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(26), P. 5351 - 5355

Published: Jan. 1, 2023

An organophotocatalyzed synthesis of polycyclic quinazolinones with a distal nitrile group is reported in the aqueous medium.

Language: Английский

---