An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction DOI Creative Commons

Yueling He,

Zhong‐Tao Yang,

Danyang Luo

и другие.

Molecules, Год журнала: 2023, Номер 28(15), С. 5734 - 5734

Опубликована: Июль 28, 2023

An oxidant-free and highly efficient synthesis of phenolic quinazolin-4(3H)-ones was achieved by simply stirring a mixture 2-aminobenzamides, sulfonyl azides, terminal alkynes. The intermediate N-sulfonylketenimine underwent two nucleophilic additions the group eliminated through power aromatization. natural product 2-(4-hydroxybenzyl)quinazolin-4(3H)-one can be synthesized on large scale under mild conditions with this method.

Язык: Английский

Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates DOI

Minglin Tao,

Feng Qin,

Kaixing Gong

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(7), С. 4199 - 4208

Опубликована: Янв. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Язык: Английский

Процитировано

15

Cu-Catalyzed Relay Functionalization of Alkenes: Diverse Synthesis of Diazidated Quinazolinones and Polycyclic Imidazoles DOI

Ji-Ming Xi,

Zhonglin Wei, Wei‐Wei Liao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

A Cu-catalyzed relay process for the preparation of diazidated quinazolinone and polycyclic imidazole derivatives in which readily available alkene-tethered substrates undergo an addition/cyclization/C(sp3)–H functionalization alkene sequences with high efficiency is described. Various functionalized N-heteropolycyclic compounds were prepared good yields a broad substrate scope. Moreover, direct azidation α-C(sp3)–H bond corresponding N-heterocycles has been demonstrated on basis mechanistic studies, provide alternative late-stage approach derivatization N-heterocyclic scaffolds.

Язык: Английский

Процитировано

1

Fe-Catalyzed Hydrocyclization of Inactivated Alkenes to Synthesize Ring-Fused 2,3-Dihydroquinazolinone DOI

Youlu Pan,

Chaonan Tang,

Zeng Xianming

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1507 - 1513

Опубликована: Янв. 22, 2025

A Fe-catalyzed hydrocyclization reaction of unactivated alkenes was developed, utilizing PhSiH3 as the hydrogen source, yielding 2,3-dihydroquinazolinone (DHQZ) derivatives in moderate to good yields. Notably, when substrate switched N-cyano-N-(2-(prop-1-en-2-yl)phenyl)benzamides, yielded only unreduced products. Mechanistic studies revealed that intramolecular addition situ formed radical alkene results formation fused ring.

Язык: Английский

Процитировано

1

Electrochemical or Photoelectrochemical Alkenylpolyfluoroalkylation of 3-Aza-1,5-dienes: Regioselective Entry to Polyfluoroalkylated 4-Pyrrolin-2-ones DOI
Xi Hu,

Minglin Tao,

Kaixing Gong

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 12935 - 12948

Опубликована: Сен. 6, 2023

An electrochemical or photoelectrochemical regioselective polyfluoroalkylation/cyclization cascade of 3-aza-1,5-dienes with sodium fluoroalkanesulfinates is presented. This protocol proceeds a broad substrate scope and good functional group tolerance under mild, oxidant-free, transition-metal-free, electrolyte-free conditions to provide 3-polyfluoroalkylated 4-pyrrolin-2-ones in one step from readily available N-vinylacrylamides, it scalable the Gram scale.

Язык: Английский

Процитировано

15

Endo/Exo-Controllable Photocyclization by EnT-SET-Switch DOI

Xian-Peng Cai,

Bin-Hong Han,

Fu-Tong Cen

и другие.

Organic Letters, Год журнала: 2023, Номер 25(16), С. 2863 - 2867

Опубликована: Апрель 17, 2023

CBZ6, a redox-neutral non-donor-acceptor-type organo-photocatalyst, presents strong reductive potential with an oxidative of -2.16 V (vs SCE). It can work as photosensitizer for both single-electron transfer and triplet energy processes. This feature enables site-selective control in the intramolecular hydroarylation acrylamides. Both 5-exo-trig 6-endo-trig cyclization products could be prepared regiospecfically under mild conditions. No transition metal, halogen-containing reagents, or additional reductant oxidant is involved. process provides concise environmentally sustainable access to series oxindoles dihydroquinolinones.

Язык: Английский

Процитировано

14

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

Xian Wu,

Ling-Li Liu,

Chengli Xiang

и другие.

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

Процитировано

5

(NH4)2S2O8 promoted tandem radical cyclization of quinazolin-4(3H)-ones with oxamic acids for the construction of fused quinazolinones under metal-free conditions DOI
Shenyuan Gao, Menglu Cai, Gang Xu

и другие.

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

Процитировано

5

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

Abuthayir Mohamathu Ghouse,

Srirama Murthy Akondi

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

Процитировано

9

Cascade Cyclization of N-Cyanamide Alkenes for the Divergent Synthesis of Azido-, Nitro-, and Alkenyl-Containing Pyrroloquinazolinones DOI
Bo Jiang, Cui Zhang,

Tai‐Gang Fan

и другие.

Organic Letters, Год журнала: 2024, Номер 26(38), С. 8028 - 8033

Опубликована: Сен. 16, 2024

Radical cascade cyclizations of

Процитировано

3

Photocatalytic Charge-Transfer Complex Enables Hydroarylation of Alkenes for Heterocycle Synthesis DOI

Ying‐Zheng Ren,

Chang-Zhen Fang,

Beibei Zhang

и другие.

Organic Letters, Год журнала: 2023, Номер 25(19), С. 3585 - 3589

Опубликована: Май 8, 2023

Here, we report a photocatalytic charge-transfer complex (CTC) strategy for one electron reduction of alkenes using thiolate as catalytic donor. This CTC system could engage hydroarylation both activated and unactivated the synthesis various heterocycles. The reactions do not require any photocatalysts or acids are easy to perform. Mechanistic studies revealed formation between alkene.

Язык: Английский

Процитировано

8