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

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(15), P. 5734 - 5734

Published: July 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.

Language: Английский

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

Minglin Tao,

Feng Qin,

Kaixing Gong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

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

Language: Английский

Citations

15

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

Ji-Ming Xi,

Zhonglin Wei, Wei‐Wei Liao

et al.

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

Published: Jan. 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.

Language: Английский

Citations

1

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

Youlu Pan,

Chaonan Tang,

Zeng Xianming

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1507 - 1513

Published: Jan. 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.

Language: Английский

Citations

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

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 12935 - 12948

Published: Sept. 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.

Language: Английский

Citations

15

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

Xian-Peng Cai,

Bin-Hong Han,

Fu-Tong Cen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2863 - 2867

Published: April 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.

Language: Английский

Citations

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

et al.

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

Citations

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

et al.

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

Citations

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, 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

Citations

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

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8028 - 8033

Published: Sept. 16, 2024

Radical cascade cyclizations of

Citations

3

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

Ying‐Zheng Ren,

Chang-Zhen Fang,

Beibei Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3585 - 3589

Published: May 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.

Language: Английский

Citations

8