Regioselective Synthesis of 2‐(Trifluoromethyl)‐3‐ethoxycarbonyl‐4‐(2‐oxo‐2‐arylethyl)‐4<i>H</i>‐chromene Derivatives by [3, 3] Sigmatropic Rearrangement

Kuchukulla, Ratnakar Reddy; Desagoni, Madhu; Narra, Srikanth Reddy; Goutham, Santhosh Kumar; Narsaiah, B.

doi:10.1002/slct.201701723

Cited by 3 publications

(3 citation statements)

References 18 publications

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“…As for the reaction mechanism, the author proposed that the reaction initiated with the activation of OH of As for the synthesis of 4-(2-oxo-2arylethyl)-4Hchromenes, Banda et al in 2017 developed an efficient method which relied on a direct electrophilic addition of hydroxyl group of 2H-chromenes 21 on aryl acetylene 27 followed by Cope rearrangement in the presence of BF 3 • Et 2 O as Lewis acid catalyst. [9] The use of 10 mol% of BF 3 • Et 2 O allowed the formation of desired products 28 in 64-85% yields in CH 2 Cl 2 at room temperature for 1-3 h (Scheme 6).…”

Section: H-chromene Hemiketals Used As the Reactantsmentioning

confidence: 99%

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Advancements in the Preparation of 4H‐Chromenes: An Overview

et al. 2023

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Functionalized 4H‐chromenes represent one class of the most important structural scaffolds in both synthetic and medicinal chemistry. They often appear in an arrange of biological natural products, pharmaceutical agents and drug candidates. The significance has stimulated the development of efficient methodologies for the synthesis of such compounds. In this review, a comprehensive discussion on different synthetic approaches to 4H‐chromenes has been presented with an emphasis on reaction features and mechanisms. Three main categories are outlined: 1) nucleophilic addition to 2H‐chromene derivatives, 2) 4H‐chromene ring formation involved cycloaddition or cyclization reactions, and 3) miscellaneous reactions.

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Section: H-chromene Hemiketals Used As the Reactantsmentioning

confidence: 99%

“…[2j] What's more, 2-amino-3-cyano-4Hchromenes are considered to exhibit strong cytotoxicity against human cancer cells. [2k] For instance, MX-58151 (9) remained activity in tumor cells resistant towards antimitotic agents, such as taxanes and Vinca alkaloids.…”

Section: Introductionmentioning

confidence: 99%

Advancements in the Preparation of 4H‐Chromenes: An Overview

et al. 2023

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“…. vi-A new efficient method for synthesizing ethyl 4-(2-oxo-2-arylethyl)-2-(trifluoromethyl)-4Hchromene was developed by using BF3.OEt2 (10 mol%) as a catalyst by [3,3] sigmatropic rearrangement [20], as demonstrated in Scheme 6. Scheme 6.…”

Section: Scheme 1 Synthesis Chromene By Ionic Liquid [Hmim]hso4 As Ca...mentioning

confidence: 99%

A Brief Review: Some Interesting Methods of Synthesis Chromene Derivatives as Bioactive Molecules

Zainab Sallal Abdulsahib,

Raied Mustafa Shakir

2023

IHJPAS

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Chromene is considered a fused pyran ring with a benzene ring, which is found in many plants and is part of many important compounds such as anthocyanidins, anthocyanins, catechins, and flavanones. These compounds are included under the headings "flavonoids" and "iso-flavonoids." These compounds are well known as bioactive molecules with wide medicinal uses. According to these pharmacokinetic characteristics, many researchers are giving more attention to this type of compound and its derivatives. Many chromene derivatives have been synthesized to study their biological effects for the treatment of many diseases. Furthermore, the researcher displayed wide interest in finding new methods for synthesizing chromene derivatives. These methods depend on utilizing a new catalyst to increase the yield of this reaction or reduce the time of the reaction. On the other hand, new methods were found by using a new reactant and a new substrate. This review will present the most recent important methods for the synthesis of chromene derivatives as well as an examination of their biological activity.

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[3,3]-Sigmatropic rearrangements: a variety of methods and recent advances

Dyachenko¹,

Baryshev²,

Nenajdenko³

2022

Usp. khim.

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Проанализированы, систематизированы и обобщены опубликованные за последние 10 лет литературные данные, касающиеся [3,3]-сигматропных перегруппировок. Перечислены основные типы [3,3]-сигматропных перегруппировок, рассмотрены оптимальные каталитические системы для различных вариантов превращений и для соединений разных классов. Приведены примеры использования таких реакций при синтезе структурно-сложных, биологически активных, природных и практически ценных веществ. Для некоторых процессов продемонстрированы механистические закономерности их протекания, а также представлены геометрия переходных состояний и структуры интермедиатов. <br> Библиография — 533 ссылки.

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Regioselective Synthesis of 2‐(Trifluoromethyl)‐3‐ethoxycarbonyl‐4‐(2‐oxo‐2‐arylethyl)‐4H‐chromene Derivatives by [3, 3] Sigmatropic Rearrangement

Cited by 3 publications

References 18 publications

Advancements in the Preparation of 4H‐Chromenes: An Overview

Advancements in the Preparation of 4H‐Chromenes: An Overview

A Brief Review: Some Interesting Methods of Synthesis Chromene Derivatives as Bioactive Molecules

[3,3]-Sigmatropic rearrangements: a variety of methods and recent advances

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