Advances in the Synthesis of Azaspiro[4.5]trienones DOI Open Access
Jing Tang, Wenkun Luo, Jun Zhou

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(9), P. 3006 - 3006

Published: Jan. 1, 2023

As one of the most important structural motifs in natural compounds and active pharmaceutical ingredients, azaspiro[4.5]trienonesderivatives have been widely used field organic synthesis due to their excellent properties biological activities.In recent years, several methods, such as transition metal involvement, visible light promotion, metal-free involvement electrochemical efficiently construct various functional groups azaspiro[4.5]trienones.The advances azaspiro[4.5]trienones are reviewed, representative substrates reaction mechanisms summarized discussed.

Language: Английский

Visible-light-induced acylation/cyclization of active alkenes: facile access to acylated isoquinolinones DOI
Yang Guo, Peng‐Fei Huang, Yu Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(18), P. 3767 - 3778

Published: Jan. 1, 2022

Nitrogen heterocycles, especially polycyclic compounds, are significant skeletons in valuable molecules. Herein, we developed an efficient and practical visible-light-induced acylation/cyclization of active alkenes with acyl oxime derivatives for constructing acylated indolo/benzimidazo-[2,1,a]isoquinolin-6(5H) ones. This reaction was compatible various functional groups a series fused indole/imidazole were prepared up to 95% yield at room temperature.

Language: Английский

Citations

10

Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters DOI Creative Commons
Pu Chen, Huawen Huang,

Qi Tan

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2667 - 2667

Published: March 15, 2023

The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed the last few decades. Among them, N–O bond cleavage esters leading to formation nitrogen-centered radicals triggers adjacent C–C produce carbon-centered free radicals, which has virtually used organic synthesis recent years. Herein, we summarized radical involving and through this special reaction form, including those from acyl ester cyclic ketoxime derivatives. These contents were systematically classified according different types. In review, after 2021 included, with emphasis on substrate scope mechanism.

Language: Английский

Citations

6

Light‐Promoted Germylation of Aryl Propiolamides/Alkynoates: Synthesis of Ge‐Containing Spiro[4.5]trienones and Vinylgermanes DOI

Yani Luo,

Leiyang Lv, Zhiping Li

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(13)

Published: May 11, 2023

Abstract The light‐promoted regioselective germylation of aryl propiolamides/alkynoates with germanium hydrides is reported. germyl‐containing spiro[4.5]trienones were obtained when N ‐arylpropiolamides used via sequential C−Ge and C−C bond formation, while alkynoates delivered the vinylgermanes radical Smiles rearrangement CO 2 release.

Language: Английский

Citations

6

Chromium-catalyzed allylic defluorinative acylation of trifluoromethyl-substituted alkenes with acyl oxime esters DOI

Hongzhang Shi,

Haiyan Dong, Chuan Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 5843 - 5850

Published: Jan. 1, 2023

A chromium-catalyzed reductive allylic defluorinative acylation of trifluoromethyl-substituted alkenes with acyl oxime esters has been developed, allowing for efficient synthesis various ketones bearing a gem -difluoroalkene unit.

Language: Английский

Citations

6

The visible-light-induced acylation/cyclization of alkynoates with acyl oximes for the construction of 3-acylcoumarins DOI
Quan Zhou,

Fang‐Ting Xiong,

Pu Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(41), P. 9012 - 9020

Published: Jan. 1, 2021

A nitrogen-centered radical-mediated carbon–carbon bond cleavage strategy for the construction of 3-acylcoumarins via visible-light-induced cascade acylation/cyclization alkynoates with acyl oxime compounds is reported.

Language: Английский

Citations

14

Visible-light-induced tandem difluoroalkylated spirocyclization of N-arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones DOI
Jinwei Yuan,

Lu Shen,

Mengyao Ma

et al.

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(9), P. 4470 - 4482

Published: Jan. 1, 2022

A visible-light-catalyzed difluoroacetylated spirocyclization of N -arylpropiolamides with ethyl bromodifluoroacetate as a CF 2 CO Et radical precursor is described using fac -[Ir(ppy) 3 ] photocatalyst.

Language: Английский

Citations

8

K2S2O8‐Mediated Access to Alkylsulfonated Spiro[4,5] Trienones from N‐Arylpropiolamides with the Insertion of Sulfur Dioxide DOI

Xin‐Qian Liu,

Peng‐Fei Huang, Biquan Xiong

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 488 - 493

Published: Dec. 23, 2023

Abstract A four‐component reaction of N ‐arylpropiolamides, Hantzsch esters, Na 2 S O 5 and water via a radical cascade cyclization process with the insertion sulfur dioxide mediated by K 8 is reported. series alkylsulfonated spiro[4,5] trienones are prepared up to 86% yield good functional group tolerance substrate applicability. Preliminary mechanism experiments indicate that carbonyl oxygen originated from water.

Language: Английский

Citations

4

Metal- and photocatalyst-free approach to visible-light-induced acylation of quinoxalinones DOI
Worawat Niwetmarin, Naiyana Saesian, Rungroj Saruengkhanphasit

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5924 - 5929

Published: Jan. 1, 2024

A transition-metal- and photocatalyst-free photochemical acylation strategy driven by the photoexcitation of an electron donor–acceptor (EDA) complex has been developed.

Language: Английский

Citations

1

Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr2 Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization DOI
Jinhui Cai,

Kaili Cen,

Hongyi Lin

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(20)

Published: June 27, 2024

Abstract Herein, a method for the assembly of biologically valuable 3‐selenospiro[4,5]decatrienones through CuBr 2 ‐catalyzed ispo ‐cyclization Se powder, boronic acids, and N ‐( p ‐methoxyaryl)propiolamides has been established. In this protocol, noble transition metal, prefunctionalized selenylation reagent, strong chemical oxidant are not employed. This feature wide substrate scope, good functional group tolerance, easy operation, employing earth‐abundant metal as catalyst green air oxidant. Furthermore, several derivatizations performed to showcase practicability our strategy.

Language: Английский

Citations

1

Photocatalytic Radical Cyclization of N-(o-Cyanobiaryl)acrylamides with Oxime Esters DOI
Yu Liu,

Shun-Dan Li,

Jian-Hong Fan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(37), P. 7628 - 7631

Published: Jan. 1, 2024

A visible-light-mediated radical cascade cyclization of N -( o -cyanobiaryl)acrylamides with oxime esters for the assembly acyl-containing pyrido[4,3,2- gh ]phenanthridines has been developed.

Language: Английский

Citations

1