Asymmetric Allylic Substitution‐Isomerization for the Modular Synthesis of Axially Chiral N‐Vinylquinazolinones DOI
Jiayu Zou, Yuying Yang,

Jun Gu

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(40)

Published: Aug. 16, 2023

Abstract Axially chiral N ‐substituted quinazolinones are important bioactive molecules, which presented in many synthetic drugs. However, most strategies toward their atroposelective synthesis mainly limited to the axially arylquinazolinone frameworks. The development of modular methods access diverse quinazolinone‐based atropisomers remains scarce and challenging. Herein, we report regio‐ ‐vinylquinazolinones via strategy asymmetric allylic substitution‐isomerization. catalysis system utilized both transition‐metal organocatalysis efficiently afford trisubstituted tetrasubstituted ‐vinylquinazolinone atropisomers, respectively. With meticulous design β‐substituted substrates, Z ‐ E ‐tetrasubstituted were obtained good yields high enantioselectivities.

Language: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

Citations

34

Regioselective synthesis of phenanthridine-fused quinazolinones using a 9-mesityl-10-methylacridinium perchlorate photocatalyst DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(30), P. 4455 - 4458

Published: Jan. 1, 2023

Herein, we demonstrate a regioselective intramolecular C-N cross-coupling for the synthesis of 14H-quinazolino[3,2-f]phenanthridin-14-one by using 9-mesityl-10-methylacridinium perchlorate as visible-light (450-470 nm) photocatalyst. The experiments with BHT, TEMPO, and Stern-Volmer quenching studies helped to rationalize radical pathway via SET mechanism.

Language: Английский

Citations

19

CsPbBr3 Perovskite Photocatalyst in Chemodivergent Functionalization of N-Methylalkanamides Using CBr4 DOI

Buddhadeb Pal,

Ashis Mathuri,

Anupam Manna

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4075 - 4079

Published: May 26, 2023

Herein we have developed a strategy for chemodivergent functionalization of N-methylalkanamides via C-Br bond activation CBr4, using an orthorhombic CsPbBr3 perovskite photocatalyst under blue LEDs (450-470 nm). The selectivity whether 5-exo-trig spiro cyclization or 6-endo-trig occurred depended on the stability radical intermediate that was formed after addition bromide to starting compound obtain 3,8-dibromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-trien-2-on 3-bromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione 3-bromo-6-(tert-butyl)-1-methyl-4-phenylquinolin-2(1H)-one.

Language: Английский

Citations

18

Visible-Light-Induced Cascade Cyclization of 3-(2-(Ethynyl)phenyl)quinazolinones to Phosphorylated Quinolino[2,1-b]quinazolinones DOI

Fan‐Lin Zeng,

Zhi-Yang Zhang,

Pengcheng Yin

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(43), P. 7912 - 7917

Published: Oct. 21, 2022

3-(2-(Ethynyl)phenyl)quinazolinones were designed and synthesized as a class of novel efficient skeletons for phosphorylation/cyclization reactions. Under visible light irradiation, series phosphorylated quinolino[2,1-b]quinazolinones (35 examples, up to 87% yield) first from 3-(2-(ethynyl)phenyl)quinazolinones diarylphosphine oxides by using 4CzIPN photocatalyst under mild conditions. This reaction was also applicable sunlight irradiation. Moreover, the efficiency could be significantly improved continuous-flow

Language: Английский

Citations

27

Asymmetric Allylic Substitution‐Isomerization for the Modular Synthesis of Axially Chiral N‐Vinylquinazolinones DOI Open Access
Jiayu Zou, Yuying Yang,

Jun Gu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(40)

Published: Aug. 16, 2023

Abstract Axially chiral N ‐substituted quinazolinones are important bioactive molecules, which presented in many synthetic drugs. However, most strategies toward their atroposelective synthesis mainly limited to the axially arylquinazolinone frameworks. The development of modular methods access diverse quinazolinone‐based atropisomers remains scarce and challenging. Herein, we report regio‐ ‐vinylquinazolinones via strategy asymmetric allylic substitution‐isomerization. catalysis system utilized both transition‐metal organocatalysis efficiently afford trisubstituted tetrasubstituted ‐vinylquinazolinone atropisomers, respectively. With meticulous design β‐substituted substrates, Z ‐ E ‐tetrasubstituted were obtained good yields high enantioselectivities.

Language: Английский

Citations

17

Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst DOI
Ashis Mathuri,

Buddhadeb Pal,

Milan Pramanik

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 10096 - 10110

Published: July 3, 2023

Herein we report a cascaded chalcogenation of aryl alkynoates or N-arylpropynamides using 9-mesityl-10-methylacridinium perchlorate as visible light photocatalyst to obtain selectively either 3-sulfenylated/selenylated coumarins spiro[4,5]trienones. In radical initiated process, the spiro-cyclization reaction was favored due presence -OMe -F substituent at para position group, which helped stabilize allylic intermediate formed during reaction. Otherwise, 6-endo-trig cyclization led coumarins. Overall, new C–S/C–Se, C–C, and C═O bonds were in single step. The Stern–Volmer quenching study, EPR experiments, ON-OFF trapping etc., understand radical-based mechanism.

Language: Английский

Citations

15

Sustainable Synthesis through Catalyst‐Free Photoinduced Cascaded Bond Formation DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(14)

Published: May 8, 2024

The beginning of photochemical reactions revolutionized synthetic chemistry through sustainable practices. This review explores cutting-edge developments in leveraging light-induced processes for generating cascaded C-C and C-hetero bonds without catalysts. Significantly, catalyst-free photoinduced methodologies have garnered considerable attention, especially the creation varied heterocyclic frameworks drug design synthesis natural products. article delves into underlying mechanisms, addresses limitations, evaluates various methodologies, emphasizing potential photocatalyst transition metal-free to enhance sustainability. Divided two sections, it covers recent strides C-heteroatom multiple bond formation reactions.

Language: Английский

Citations

5

Regioselective [3+2]‐Spiroannulation and [4+n]‐Annulation Approaches through Activation of C−H Bond Facilitated by Ru(II) as Catalyst: Role of Solvent Selectivity DOI
Rahul Dev Mandal, Anindita Sarkar, Dwaipayan Das

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1863 - 1876

Published: Feb. 21, 2024

Abstract Ru(II)‐catalyzed and solvent‐switched [3+2]‐spiroannulation [4+n] (n=1, 2, 3) annulations of 2‐aryl quinazolinone or 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with ynones alkynyl alcohol 1,3‐diynes under mild reaction conditions have been analyzed. These reactions take place in the presence appropriate solvent features a redox‐neutral pathway. Ynone serves as an ‘atypical one‐carbon unit’ [4+1] annulation generates tetrasubstituted carbon center bearing diverse heterocycles through [3+2] strategies. Post transformations synthesized spiro‐products augments potential developed methodology.

Language: Английский

Citations

4

An Iron‐Catalyzed Three‐Component Radical Cascade Cyclization to Access Cyanoalkylsulfonyl Quinolino‐Quinazolinones DOI

Abuthayir Mohamathu Ghouse,

Uppalam Tarun,

Bathula Maheswari

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2456 - 2460

Published: March 21, 2024

Abstract An iron(II)‐catalyzed cascade reaction, involving cyanoalkylsulfonylation and cyclization, has been devised to enable the synthesis of functionalized sulfonylated quinolino‐quinazolinone alkyl nitriles. This three‐component radical transformation exhibits excellent chemo‐ regioselectivity while functioning without need for external oxidizing or reducing agents. The cost‐effectiveness this catalytic system, together with its broad substrate application, which includes drug molecule derivatives, make approach efficient adaptable.

Language: Английский

Citations

4

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation DOI Creative Commons
Sourav Behera, Shyamal Kanti Bera, Francesco Basoccu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2035 - 2043

Published: Feb. 8, 2024

Abstract Our research has demonstrated that mechanochemical activation is more effective with solid reagents. We have showcased the practicality of Bertagnini's salts, also called aldehyde‐bisulfite adducts, which are crystalline, simplifying preparation and storage. These salts stable substitutes for liquid aldehydes ketones been employed in reductive amination, synthesizing aza‐heterocycles hydrazones within mechanochemistry. The technique‘s effectiveness broadens substrate scopes, simplifies purification, reduces reaction times, yields desired products ranging from 38–91%. Additionally, thermal stability bisulfite adducts confirmed through TGA (Thermogravimetric analysis) analysis.

Language: Английский

Citations

3