Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization DOI Open Access
Peng Liu,

Fuming Zhong,

Lihao Liao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4019 - 4019

Published: Jan. 1, 2023

Spirocyclohexadienones are not only widely present in bioactive molecules, but also act as key synthetic intermediates for the synthesis of natural products.Owing to great importance these compounds, their efficient has drawn considerable attention from chemists.In particular, there many reports about spirocyclohexadienone derivatives via alkyne-involving dearomatization past few years.The success reactions benefits reaction mode: activation alkyne π bond by radicals, electrophiles, or metal catalysts under conditions photocatalysis, electrocatalysis, chemical oxidation, and then subsequent process.The advances electron-deficient, electron-ordinary, electron-rich alkynes-participated phenolic realize construction recent five years systematically summarized.During discussion, used triggering ways subdivided.At last, prospects this field discussed.

Language: Английский

Silyl Radical Generation from Silylboronic Pinacol Esters through Substitution with Aminyl Radicals DOI

Hongyan Lan,

Xiangyu Huo,

Ying‐Gang Jia

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(5), P. 1011 - 1016

Published: Jan. 30, 2024

A novel strategy was developed to generate silyl radicals from silylboronic pinacol esters (SPEs) through nucleohomolytic substitution of boron with aminyl radicals. We successfully applied this obtain diverse organosilicon compounds using SPEs and N-nitrosamines under photoirradiation without any catalyst. The ability access offers a new perspective for chemists rapidly construct Si–X bonds.

Language: Английский

Citations

11

ipso-Cyclization of unactivated biaryl ynones leading to thio-functionalized spirocyclic enones DOI
Chada Raji Reddy,

Uprety Ajaykumar,

Amol D. Patil

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(31), P. 6379 - 6388

Published: Jan. 1, 2023

Dearomative ipso -annulation of unactivated biaryl ynones using AgSCN/AgSCF 3 as the radical source in presence CAN DMSO is disclosed.

Language: Английский

Citations

17

Radical Three-Component Nitro Spiro-Cyclization of Unsaturated Sulfonamides/Amides to Access NO2-Featured 4-Azaspiro[4.5]decanes DOI

Changyou Guo,

Li‐Jun Li,

Qinqin Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3069 - 3074

Published: April 1, 2024

Free radical three-component nitration/spirocyclization of unsaturated sulfonamides/amides with tert-butyl nitrite was developed for the construction diverse NO2-revised 4-azaspiro[4.5]decanes. This tandem system featured metal-free participation, simple operation, good selectivity/yields, and a green/low-cost O source. Meanwhile, one nitro-containing complex molecule scaled-up operation were performed well to test synthetic potential cascade reaction. Isotopic labeling, inhibition experiments, DFT analysis carried out gain insight into reaction process.

Language: Английский

Citations

6

Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with chloroalkanes DOI

Hongxun Zhou,

Lijun Li,

Qinqin Yan

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(29), P. 3938 - 3941

Published: Jan. 1, 2024

A metal-free radical bicyclization of chloralkanes and 1,6-enynes produces various polychlorinated/chlorinated polyheterocycles.

Language: Английский

Citations

5

Recent advances in the synthesis of benzimidazolo[2,1-a]isoquinoline-6(5H)-one derivatives from N-methylacryloyl-2-arylbenzimidazoles DOI

Qinggang Mei,

Qinghan Li

Tetrahedron, Journal Year: 2024, Volume and Issue: 160, P. 134050 - 134050

Published: May 25, 2024

Language: Английский

Citations

4

Metal- and additive-free radical-triggered nitration/cyclization to construct indolo[2,1-α]isoquinoline and benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives usingt-BuONO as nitro reagents DOI
Yucai Tang,

Yiting Yang,

Qian Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(25), P. 5254 - 5264

Published: Jan. 1, 2023

An efficient metal- and additive-free nitro radical-triggered addition/cyclization for the synthesis of nitro-substituted indolo[2,1- α ]isoquinoline benzimidazo[2,1- a ]isoquinolin-6(5 H )-one derivatives has been developed.

Language: Английский

Citations

10

Metal/Peroxide‐Free [5 + 1] Cyclization of 2‐Vinylanilines with tert‐Butyl Nitrite to Access Diverse Cinnolines DOI Open Access
Huaqing Liu,

Qinqin Yan,

Zexuan Liu

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(6)

Published: Feb. 1, 2025

Abstract An efficient metal/peroxide‐free [5 + 1] cyclization of 2‐vinylanilines with TBN was realized to access various cinnolines high yields. In addition, benzo[ e ]pyrrolo[2,1‐c][1,2,4]triazines could also be obtained by using 2‐(1 H ‐pyrrol‐1‐yl)anilines as the raw materials. This cascade system selected common/low‐cost tert ‐butyl nitrite N1 source, which performed broad substrate scopes/simple operation/mild conditions/available scaled up 1 mmol.

Language: Английский

Citations

0

Visible Light Promoted Brominative Dearomatization of Biaryl Ynones to Spirocycles DOI

Barnali Roy,

Puspendu Kuila,

Debayan Sarkar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 10925 - 10945

Published: July 17, 2023

Bromine induced spiro cyclization of biaryl ynones facilitated the synthesis spiro[5,5]trienones suitable for extended functionality at C(3') position. Herein, a step-economic photo-oxidative brominative carbannulation employing ammonium bromide and riboflavin tetraacetate (RFTA) has been developed. The reactivity between distal phenyl C-H activated ortho-annulation dearomative ipso-annulation is well exemplified. eminent features methodology include metal-free, external additive free, low-loading photocatalyst (0.1 mol %), use simple precursor.

Language: Английский

Citations

6

Recent advances in radical thiocyanation cyclization or spirocyclization reactions DOI

Qinqin Yan,

Shiliu Chen,

Jie Fan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9112 - 9122

Published: Jan. 1, 2023

Organic thiocyanates are valuable biological moities and drug-building blocks. They can also transform effectively into thioethers, thiols, alkynyl thiocarbamates in synthetic chemistry. With respect to the merits of thiocyanates, many chemists our research team have developed diverse strategies access SCN-revised heterocycles/spirocycles via an effective radical cyclization process. Hence, this review article first describes importance/application thiocyanates. Subsequently, it summarizes reaction conditions, substrate scopes, plausible mechanism, respectively, excellent work stated above.

Language: Английский

Citations

6

Synthesis of Indenones via Persulfate Promoted Radical Alkylation/Cyclization of Biaryl Ynones with 1,4-Dihydropyridines DOI Creative Commons
Wanwan Wang, Lei Yu

Molecules, Journal Year: 2024, Volume and Issue: 29(2), P. 458 - 458

Published: Jan. 17, 2024

The oxidative radical cascade cyclization of alkynes has emerged as a versatile strategy for the efficient construction diverse structural units and complex molecules in organic chemistry. This work reports an alkyl initiated 5-exo-trig biaryl ynones with 1,4-dihydropyridines to selectively synthesize indenones.

Language: Английский

Citations

1