Radical-mediated photoredox hydroarylation with thiosulfonate

Chemical Communications, Год журнала: 2023, Номер 59(19), С. 2767 - 2770

Опубликована: Янв. 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.

Язык: Английский

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

Organic Letters, Год журнала: 2023, Номер 25(10), С. 1683 - 1688

Опубликована: Март 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.

Язык: Английский

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

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 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.

Язык: Английский

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

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(22), С. 6290 - 6294

Опубликована: Янв. 1, 2022

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

Язык: Английский

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

Chemical Communications, Год журнала: 2024, Номер 60(18), С. 2556 - 2559

Опубликована: Янв. 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.

Язык: Английский

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(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, Год журнала: 2024, Номер 22(11), С. 2241 - 2251

Опубликована: Янв. 1, 2024

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

Язык: Английский

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

Chemical Communications, Год журнала: 2024, Номер 60(35), С. 4687 - 4690

Опубликована: Янв. 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.

Язык: Английский

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

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5861 - 5874

Опубликована: Апрель 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.

Язык: Английский

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

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134497 - 134497

Опубликована: Янв. 1, 2025

Язык: Английский

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

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(26), С. 5351 - 5355

Опубликована: Янв. 1, 2023

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

Язык: Английский

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