Divergent Sc(OTf)3‐Catalyzed Tandem Cyclization of o‐Hydroxyphenyl Enaminones with 1,3,5‐Triazinanes: Access to C3‐Aminomethyl Chromones and Tetrahydropyrimidines DOI Open Access

Siyang Han,

Chengcheng Fang, Sifeng Li

и другие.

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

Опубликована: Окт. 9, 2024

Abstract A Sc(OTf) 3 ‐catalyzed tandem cyclization reaction of o ‐hydroxyphenyl enaminones with 1,3,5‐triazinanes has been developed to generate two distinct annulated products in moderate good yields, which is dominated by the electronic characteristics 1,3,5‐triazinanes. The 1,3,5‐triaryl‐1,3,5‐triazinane reacted as C−N synthon produce C3‐aminomethyl chromone, while 1,3,5‐trialkyl‐1,3,5‐triazinane acted C−N−C−N synthons deliver N , ‐dialkyl tetrahydropyrimidine a free hydroxyl group.

Язык: Английский

Photobiocatalytic Strategies for Organic Synthesis DOI
Megan A. Emmanuel, Sophie G. Bender,

Catherine Bilodeau

и другие.

Chemical Reviews, Год журнала: 2023, Номер 123(9), С. 5459 - 5520

Опубликована: Апрель 28, 2023

Biocatalysis has revolutionized chemical synthesis, providing sustainable methods for preparing various organic molecules. In enzyme-mediated most reactions involve molecules operating from their ground states. Over the past 25 years, there been an increased interest in enzymatic processes that utilize electronically excited states accessed through photoexcitation. These photobiocatalytic a diverse array of reaction mechanisms are complementary to one another. This comprehensive review will describe state-of-the-art strategies photobiocatalysis synthesis until December 2022. Apart reviewing relevant literature, central goal this is delineate mechanistic differences between general employed field. We organize based on relationship photochemical step and transformations. The include studies, substrate scopes, protein optimization strategies. By clearly defining mechanistically-distinct chemistry, we hope illuminate future synthetic opportunities area.

Язык: Английский

Процитировано

139

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

и другие.

Chinese Chemical Letters, Год журнала: 2023, Номер 35(2), С. 108977 - 108977

Опубликована: Авг. 26, 2023

Язык: Английский

Процитировано

64

Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones DOI

Mingshuai Zhang,

Meichen Liu,

Yuetong Qiu

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2363 - 2369

Опубликована: Март 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Язык: Английский

Процитировано

13

Visible-light-driven EDA complex-promoted cascade cyclization to construct 4-cyanoalkyl isoquinoline-1,3-diones DOI

Dong‐Liang Zhang,

Zhanggao Le,

Qing Li

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(21), С. 2958 - 2961

Опубликована: Янв. 1, 2024

Visible-light-driven EDA complex-promoted ring-opening of cycloketone oxime esters to synthesise various 4-cyanoalkylated isoquinoline-1,3-diones with acryloylbenzamides was developed.

Язык: Английский

Процитировано

10

Cascade in Situ Iodination, Chromone Annulation, and Cyanation for Site-Selective Synthesis of 2-Cyanochromones DOI
Yan Lin, Jie‐Ping Wan, Yunyun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 4017 - 4023

Опубликована: Март 2, 2023

A facile cascade reaction for the site selective synthesis of 2-cyanochromones is described. By using simple o-hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K4[Fe(CN)6]3·3H2O) as starting materials I2/AlCl3 promoters, products are furnished via tandem chromone ring formation C–H cyanation. The in situ 3-iodochromone a formal 1,2-hydrogen atom transfer (HAT) process account unconventional selectivity. In addition, 2-cyanoquinolin-4-one has been realized by employing corresponding 2-aminophenyl enaminone substrate.

Язык: Английский

Процитировано

23

Metal-free synthesis of difluoro/trifluoromethyl carbinol-containing chromones via tandem cyclization of o-hydroxyaryl enaminones DOI

Longhui Wu,

Xia Liu,

Zhao-Wen Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(46), С. 9236 - 9241

Опубликована: Янв. 1, 2023

A convenient and efficient method for the synthesis of difluoro/trifluoromethyl carbinol-containing chromone derivatives has been developed.

Язык: Английский

Процитировано

13

An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones DOI
Liu‐Liang Mao, Yunyun Liu, Jie‐Ping Wan

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110784 - 110784

Опубликована: Дек. 1, 2024

Язык: Английский

Процитировано

5

Electrochemical Decarboxylative Addition of N‐Aryl Glycines to Enaminones: Access to C3‐Aminomethyl Chromones DOI

Siyang Han,

Chengcheng Fang,

Yaoge Zhang

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(28)

Опубликована: Май 1, 2024

Abstract An electrochemical decarboxylative addition of N ‐substituted glycines to enaminones has been developed and conducted under oxidant‐, catalyst‐, light‐free conditions in acetonitrile at room temperature by using electron as the traceless oxidant, which provided a green approach access C3‐aminomethyl chromones. The resulting products were formed through radical addition/oxidation/cyclization or electrophilic addition/cyclization pathway could act valuable building blocks construct polysubstituted pyrimidine derivatives.

Язык: Английский

Процитировано

4

Visible light-mediated synthesis of quinazolinones from benzyl bromides and 2-aminobenzamides without using any photocatalyst or additive DOI
Sheng Huang, Liang Jin, Yufeng Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(4), С. 784 - 789

Опубликована: Дек. 20, 2023

The synthesis of quinazolinones via a visible light-mediated reaction benzyl bromides with 2-aminobenzamides is reported, and the HBr generated during first step promoted subsequent step.

Язык: Английский

Процитировано

9

Electrochemical-induced solvent-tuned selective C(sp3)–H bond activation towards the synthesis of C3-functionalized chromone derivatives DOI
Ying Gao, Mingxu Wang, Jingxian Sun

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(38), С. 5050 - 5053

Опубликована: Янв. 1, 2024

An unprecedented solvent-tuned electrochemical method for selective C(sp

Язык: Английский

Процитировано

3