Metal-Free Synthesis and Photophysical Properties of 1,2,4-Triarylpyrroles

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 86(1), P. 110 - 127

Published: Dec. 2, 2020

A three-component reaction has been developed for the construction of multiaryl-substituted pyrrole derivatives from arylketones, amines, and nitrovinylarenes under metal-free conditions. Hence, homologous 1,2,4-triaryl-substituted products were obtained in good to high yields. Furthermore, 2,3,5-triaryl-substituted pyrroles selectively formed absence nitrovinylarenes. The photophysical properties some have investigated show aggregation-induced emission (AIE) activity.

Language: Английский

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Synthesis of pyrrolidin-2-ylidenes and pyrrol-2-ylidenes via 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides to nitrostyrenes

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(25), P. 5265 - 5273

Published: Jan. 1, 2023

Diastereoselective formation of pyrrolidene-2-ylidenes by the Huisgen reaction hydrogen-bond-assisted azomethine ylides with β-bromo-β-nitrostyrenes is reported.

Language: Английский

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Ningalins, Pyrrole‐Bearing Metabolites Isolated from Didemnum spp. Synthesis and MDR‐Reversion Activity in Cancer Therapy

Chemistry & Biodiversity, Journal Year: 2023, Volume and Issue: 21(1)

Published: Nov. 28, 2023

Abstract Multi‐Drug Resistance (MDR) is one of the most frequent problems observed in course cancer chemotherapy. Cells under treatment, tend to develop survival mechanisms drug‐action thus generating drug‐resistance. One important mechanism get it over expression P‐gp glycoprotein, which acts as an efflux‐pump releasing drug outside cell. A strategy for a succesfull treatment consists co‐administration compound that against and another cell during Ningalins are pyrrole‐containing naturally occurring compounds isolated mainly from marine tunicate Didemnum spp also they some top reversing agents MDR acting on P‐gp. Considering relevance displayed these alkaloids or their core therapy, all total synthesis described date members ningalins family reviewed herein.

Language: Английский

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Developments and applications of α-bromonitrostyrenes in organic syntheses

RSC Advances, Journal Year: 2024, Volume and Issue: 14(21), P. 14835 - 14846

Published: Jan. 1, 2024

In this work, we have described the use of α-bromonitrostyrenes in synthesis a wide variety carbocyclic and heterocyclic compounds under organocatalysis, metal catalysis, base-catalysis systems as well catalyst-free reactions.

Language: Английский

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A mild one-pot synthesis of 2-iminothiazolines from thioureas and 1-bromo-1-nitroalkenes

RSC Advances, Journal Year: 2021, Volume and Issue: 11(4), P. 2221 - 2225

Published: Jan. 1, 2021

A mild method to access functionalized 2-iminothiazolines in a facile and efficient manner has been developed.

Language: Английский

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Three-Membered Ring Systems

Progress in heterocyclic chemistry, Journal Year: 2019, Volume and Issue: unknown, P. 119 - 142

Published: Oct. 13, 2019

Language: Английский

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Research Progress on Reactions Involving β-Nitrostyrene

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4168 - 4168

Published: Jan. 1, 2023

β-Nitrostyrene has a variety of biological activities and is also an important intermediate in organic synthesis, which can participate chemical reactions due to its active properties, attracted extensive attention from researchers.The involving nitrostyrene compounds recent years are summarized, the reaction divided into denitrification carbon-carbon double bonds according sites, expecting provide reference for new with β-nitrostyrene as substrates.Keywords β-nitrostyrene; denitrogenation reaction; carbon bond β-硝基苯乙烯是重要的有机化合物, 广泛存在于具 有多种生物活性的化合物结构和药物分子中, 其本身也 具有抑制人端粒酶 [1] 、杀菌 [2][3] 及抗肿瘤 [4][5] 等活性.近年 来, 其在有机合成方向的应用也越来越被重视.β-硝基苯乙烯类化合物因兼具硝基和碳碳双键而 拥有较为活泼的性质, 可参与多种类型的反应.根据文 献调研, 目前尚无相关专题综述对 β-硝基苯乙烯类化合 物参与的反应进行归纳总结.最近几年该类化合物的应 用策略越来越多, 因此, 很有必要对其进行梳理, 以期 为从事有机合成及相关领域的研究者提供有益的借鉴 和参考.以 β-硝基苯乙烯类化合物为底物的反应主要可 以分为脱硝基反应和碳碳双键参与的反应.本文将从以 上两种反应方式对近年来的重要相关文献进行综述, 并 简要介绍其反应特点和反应机理. 脱硝基反应β-硝基苯乙烯类化合物分子结构中, 由于存在强吸 电子基团硝基, 使与之相连的双键 π 电子云发生极化, 不仅能够脱硝基构建各种环状骨架 [6][7][8] , 亦可转化成新 的官能团 [9][10] 生成不同的化合物.1.1 脱硝成环 1.1.1脱硝基形成 C 环化合物 以 β-硝基苯乙烯为原料能够合成各种碳环化合物.2016 年, Swamy 课题组 [11] 报道了 Pd(OAc) 2 催化的内炔 烃与硝基苯乙烯制备 2,3-二取代茚酮的反应.环化反应 通过催化剂与硝基苯乙烯的金属转移和炔烃的插入进 行, 硝基苯乙烯基团的高亲电性为 C-H 和 C-C 裂解 环化提供了条件.该反应以中等至良好的产率和高区域 选择性进行(Eq.1).

Language: Английский

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Synthesis and structure of new β-functionalized gem-bromonitroethenes — 2-arylsulfanyl- and 2-aryloxy-3-bromo-3-nitroacrylates

Russian Chemical Bulletin, Journal Year: 2020, Volume and Issue: 69(11), P. 2191 - 2197

Published: Nov. 1, 2020

Language: Английский

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Thermal vs. Visible-Light Photoredox-Catalyzed Cascade Radical Cyclization Involving SO2 Fixation to Access 6-Alkylsulfonylmethyl Phenanthridines

Published: Dec. 22, 2023

Convenient access to 6-alkylsulfonylmethyl phenanthridines has been demonstrated both under thermal and visible-light photoredox-catalyzed conditions. A cascade of radical cyclization is triggered on exposure biphenyl vinyl azides the in-situ generated alkyl sulfonyl radicals from 4-substituted Hanztsch esters in presence an SO2 surrogate. Transition metal-free, mild reaction conditions, broad substrate scope constitute some highlights approach. Also, synthetic utility accessed demonstrated.

Language: Английский

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Five-membered ring systems: pyrroles and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2021, Volume and Issue: unknown, P. 193 - 240

Published: Jan. 1, 2021

Language: Английский

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