Transition-Metal-Free Radical Phosphorylation/Cyclization of Unactivated Alkenes: Access to Phosphine-Containing Quinazolinones DOI

shenyuan gao,

Jia Guo, Jianhai Yang

и другие.

Опубликована: Янв. 1, 2023

A new cascade radical addition/cyclization of unactivated alkenes and phosphine oxides has been developed. wide variety bioactive phosphine-containing quinazolinones were obtained in up to 91.3% yield for 29 examples under transition-metal-free conditions. This protocol represents an environmentally friendly efficient way build excellent yields mild conditions with a broad substrate scope high atomic economy.

Язык: Английский

Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones DOI Creative Commons
Jia-Jun Tang, Mengyang Zhao,

Ying-Jun Lin

и другие.

Molecules, Год журнала: 2024, Номер 29(5), С. 997 - 997

Опубликована: Фев. 25, 2024

The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple practical method the synthesis amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through carbamoyl-radical-triggered cascade cyclization N3-alkenyl-tethered quinazolinones. Notably, carbamoyl radical generated in situ from oxidative decarboxylative process oxamic acids presence (NH4)2S2O8.

Язык: Английский

Процитировано

2
Visible-light-induced cascade radical cyclization for the synthesis of amide-functionalized fused quinazolinones DOI
Shenyuan Gao, Gang Xu, Jianhai Yang

и другие.

Tetrahedron, Год журнала: 2024, Номер 159, С. 134027 - 134027

Опубликована: Май 8, 2024

Язык: Английский

Процитировано

2
Acid-catalyzed radical tandem alkylation/cyclization of unactivated alkenes with ketones: Access to ketoalkyl-substituted quinazolinone derivatives DOI

Jian-Li Wu,

Meng Yan,

Lulu Fan

и другие.

Tetrahedron, Год журнала: 2024, Номер 162, С. 134085 - 134085

Опубликована: Июнь 11, 2024

Язык: Английский

Процитировано

2
Greener Synthesis of Pyrroloquinazoline Derivatives: Recent Advances DOI
Natália M. Moreira, Jhonathan R. N. dos Santos, Arlene G. Corrêa

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(35)

Опубликована: Май 26, 2022

Abstract Quinazoline derivatives draw attention from a synthetic and medicinal chemistry point of view, given the wide range biological activities already described. This class fused N ‐heterocyclic compounds has also shown its importance potential pharmacological application. Review covers contributions reported in last ten years for synthesis pyrroloquinazoline derivatives, focusing on greener protocols to obtain these adducts, such as multicomponent reactions, photocatalysis, microwaves, electrosynthesis among others.

Язык: Английский

Процитировано

7
Mn-Catalyzed Electrooxidative Radical Cascade Cyclization for the Synthesis of 6-Phosphorylated Quinoxalino[2,1-b]quinazolin-12-ones DOI
Huanping Xie,

Jiongjiong Duan,

Yi Cao

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 12, 2024

Due to their important potential medicinal value, chemists are pursuing mild and efficient methods synthesize structurally diverse quinazolinone derivatives. In this paper, a series of isocyano-tethered

Язык: Английский

Процитировано

1
Photocatalyst-Free, Visible-Light-Mediated C–H Perfluoroalkylation of Quinazolin-4(3H)-ones with perfluoroalkyl Iodides DOI
Corinne Fruit, Thomas Delouche,

Abdoul Gadiry-Diallo

и другие.

Synthesis, Год журнала: 2023, Номер 55(21), С. 3670 - 3684

Опубликована: Март 14, 2023

Abstract A practical and sustainable photocatalyst-free protocol for photoinduced synthesis of perfluoroalkylated quinazolin-4(3H)-ones is described starting from quinazolin-4(3H)-ones. wide range substituted or fused-quinazolinones found to be compatible, providing the corresponding mono- bis-perfluoroalkylated compounds in moderate yields. This visible-light-mediated C–H perfluoroalkylation allows an environmentally friendly straightforward access array unprecedented functionalized quinazolinone scaffolds, presenting attractive features drug discovery. Control experiments demonstrated that a radical mechanism involved reaction mechanism.

Язык: Английский

Процитировано

1
Metal-free Synthesis of 1,1-Dimethyl-2,2,2-trifluoroethyl Substituted Quinazolinones via Tandem Radical Cyclization of Quinazolin-4(3H)-ones with 3,3,3-Trifluoro-2,2-dimethylpropanoic acid DOI
Shenyuan Gao, Menglu Cai,

Xiaozhong Wang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(31), С. 6376 - 6384

Опубликована: Янв. 1, 2024

A metal-free (NH

Язык: Английский

Процитировано

0
Visible-Light-Mediated Photoredox Radical Cyclization Reaction with Alkyl Boronic Acids Using Molecular Oxygen as a Sole Oxidant DOI
Xia Wang, Qingwen Gui,

Xuan-Lin Qin

и другие.

Synlett, Год журнала: 2024, Номер unknown

Опубликована: Окт. 7, 2024

Abstract Indolo[2,1-b]quinazolin-12(6H)-one derivatives are prevalent in many synthetic intermediates, pharmaceuticals, and organic materials. Herein, we developed a photoredox radical cascade cyclization reaction that uses visible light as the primary energy input to promote reaction, leading series of indolo[2,1-b]quinazolin-12(6H)-one under oxygen conditions.

Язык: Английский

Процитировано

0
Transition-Metal-Free Radical Phosphorylation/Cyclization of Unactivated Alkenes: Access to Phosphine-Containing Quinazolinones DOI

shenyuan gao,

Jia Guo, Jianhai Yang

и другие.

Опубликована: Янв. 1, 2023

A new cascade radical addition/cyclization of unactivated alkenes and phosphine oxides has been developed. wide variety bioactive phosphine-containing quinazolinones were obtained in up to 91.3% yield for 29 examples under transition-metal-free conditions. This protocol represents an environmentally friendly efficient way build excellent yields mild conditions with a broad substrate scope high atomic economy.

Язык: Английский

Процитировано

0