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

Selectfluor-Mediated Electrophilic Annulation of 2-Alkynyl Biaryls with Diorganyl Diselenides DOI

Qing-Xia Luo,

Hong‐Tao Ji,

Yuhan Lu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 16790 - 16796

Published: Nov. 28, 2023

A general and efficient method for the synthesis of various selanyl phenanthrenes/polycyclic heteroaromatics through electrophilic annulation 2-alkynyl biaryls with diorganyl diselenides under metal-free mild conditions was established. The sulfanyl phenanthrene also obtained in moderate yields.

Language: Английский

Citations

22
Selectfluor-Mediated Regioselective C-3 Alkoxylation, Amination, Sulfenylation, and Selenylation of Quinoxalin-2(1H)-ones DOI

Sonam Sonam,

Vikki N. Shinde,

Krishnan Rangan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2344 - 2357

Published: Feb. 3, 2023

A Selectfluor-promoted oxidative coupling of quinoxalin-2(1H)-ones with alcohols, amines, thiols, and selenols leading to the formation C-O, C-N, C-S, C-Se bonds has been developed. The protocol provided good excellent (53-95%) yields a wide range decorated alkoxy, alkylamino, alkylthio, arylselenyl groups at C3-position under metal- photocatalyst-free conditions. reaction is believed proceed through radical pathway. broad substrate scope including bioactive molecules, mild conditions, readily available partners, high yields, scalability, step-economy, conditions are highlighting features method. synthetic utility developed was demonstrated by gram-scale synthesis, C3-alkoxylation quinoxaline-2(1H)-one natural synthesis aldose reductase (ALR2) inhibitor histamine-4 receptor antagonist in yields.

Language: Английский

Citations

17
Recent Advancement on Selectfluor Mediated Synthesis of Heterocyclic Molecules DOI Open Access
Sukanya Das, Rudra Narayan Das, Tapas Ghosh

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 16, 2025

Abstract Selectfluor, [1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)], is a highly valuable reagent in contemporary chemistry, serving not only as an electrophilic fluorinating agent but also effective catalyst the synthesis of various pharmaceutically relevant heterocycles. This review article seeks to present comprehensive overview significant heterocyclic ring formations facilitated by selectfluor. Both metal‐free and metal‐catalyzed recent advancement on selectfluor mediated cyclisation processes are discussed this mainly over last eight years (2017‐April 2024).

Language: Английский

Citations

0
Copper(ii)-catalyzed oxidative ipso-annulation of N-arylpropiolamides and biaryl ynones with 1,3-diketones: construction of diketoalkyl spiro-trienones DOI
Chada Raji Reddy, Dattahari H. Kolgave,

Uprety Ajaykumar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(34), P. 6879 - 6889

Published: Jan. 1, 2022

An unprecedented copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, which enables the assembly diketoalkylated spiro[4.5]trienones involving oxidative dearomatization in presence ammonium persulfate [(NH4)2S2O8] as oxidant. This protocol was extended to biaryl ynones, efficiently affording spiro[5.5]trienones good yields. The significance diketoalkyl functionality illustrated by further transformation into 3-pyrazoyl spiro-trienone, a structurally unique motif.

Language: Английский

Citations

18
Selectfluor-mediated tandem cyclization of enaminones with diselenides toward the synthesis of 3-selenylated chromones DOI Creative Commons

Ji-Hong Xia,

Qian Chen, Jinwei Yuan

et al.

RSC Advances, Journal Year: 2023, Volume and Issue: 13(38), P. 26948 - 26959

Published: Jan. 1, 2023

A practical and metal-free approach for the regioselective selenation of chromones employing Selectfluor reagent under mild conditions is described. The developed method suitable a wide substrate scope affords 3-selenylated in good to excellent yield with high selectivity. An ionic mechanism proposed this transformation. Furthermore, application potassium thiocyanate enaminones synthesis thiocyano transformation also successful.

Language: Английский

Citations

6
Recent Developments in the Synthesis of Organoselenium Compounds Based on the Reactions of Organic Diselenides with Acetylenes DOI Open Access
М. В. Мусалов, В. А. Потапов, М. В. Мусалова

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(10), P. 1369 - 1369

Published: Oct. 15, 2023

The last decade has witnessed significant progress in the development of novel synthetic methods for preparation a variety new functionalized and condensed compounds via reactions organic dichalcogenides with acetylenic derivatives. present review highlights recent developments synthesis organoselenium based on diselenides acetylenes over past few years. discussion mainly focuses literature data 5 It is worth noting that lion’s share this material devoted to catalytic electrophile-mediated aromatic compounds, containing triple bond nucleophilic functional groups.

Language: Английский

Citations

6
Visible-Light-Induced Intramolecular Tandem Cyclization of Unactivated Indoloalkynes for the Synthesis of Sulfonylated and Selenylated Indolo[1,2-a]quinolines DOI
Shouren Zhang, Jinwei Yuan,

Guangchao Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11712 - 11727

Published: Aug. 2, 2023

A convenient and efficient visible-light-induced method has been developed for the construction of sulfonated selenylated indolo[1,2-a]quinolines through sulfonyl or selenyl radical-initiated tandem cyclization unactivated alkynes with sodium sulfinates diaryl diselenides under mild conditions. This protocol, which simply utilizes visible light as safe eco-friendly energy source an inexpensive nontoxic organic dye a photocatalyst without aid external photocatalyst, provides various sulfonyl- selenyl-containing in moderate to good yields.

Language: Английский

Citations

5
Synthesis of 9,10‐Bis(organochalcogenyl)phenanthrenes by Cyclization of (Biphenyl‐2‐alkyne)chalcogenides DOI
Paola S. Hellwig, Helen A. Goulart,

Jonatan S. Guedes

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 26, 2024

Abstract A regioselective, operationally simple and scalable protocol was developed for the synthesis of 9,10‐bis(organochalcogenyl)phenanthrenes seleno‐spiro[cyclohexane‐1,1′‐indene]‐2,5‐dien‐4‐ones through cyclization (biphenyl‐2‐alkyne)chalcogenides. The reaction occurs in presence diorganyl diselenides, Oxone® as a green oxidizing agent, acetonitrile at 80 °C. In this study, 20 compounds were obtained yields up to 97 % short times (1–4 h).

Language: Английский

Citations

1
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

Citations

3
Direct and Regioselective C−H Selenylation of 4‐Aminocoumarin Derivatives Mediated by Selectfluor® DOI
Andrei L. Belladona, Marina Cardoso Dilelio, Roberta Cargnelutti

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(9)

Published: Feb. 28, 2023

Abstract A mild and regioselective approach to the direct selenylation of 4‐( N ‐substituted‐amino)‐ 2H ‐chromen‐2‐ones employing Selectfluor® diorganyl diselenides has been developed. The reactions were carried out under metal‐free conditions, without need for special devices, using NaHCO 3 as a base at room temperature air. This suitable wide substrate scope affording 3‐selenyl‐4‐( in good excellent yields.

Language: Английский

Citations

1