Highly Chemoselective Nickel-Catalyzed Three-Component Cross-Trimerization between Two Distinct Terminal Alkynes and an Internal Alkyne

A new type lead-free Pd–Cu2O nanocomposite catalyst shows “double” selectivities for hydrogenation of alkynes: only terminal alkynes hydrogenated and only alkenes produced, i.e. no internal alkyne is hydrogenated.

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Vinylation of Carbonyl Oxygen in 4-Hydroxycoumarin: Synthesis of Heteroarylated Vinyl Ethers

Synthesis ◽

10.1055/s-0037-1610696 ◽

2019 ◽

Vol 51 (11) ◽

pp. 2371-2378 ◽

Cited By ~ 1

Author(s):

Rana Chatterjee ◽

Sougata Santra ◽

Grigory Zyryanov ◽

Adinath Majee

Keyword(s):

Carbonyl Oxygen ◽

Terminal Alkynes ◽

Vinyl Ethers ◽

Hydroxy Coumarin ◽

Internal Alkyne

The unique nucleophilic character of the carbonyl oxygen of 4-hydroxy coumarin has been observed by the BF3·OEt2 catalyzed reaction of 4-hydroxycoumarin and alkynes. The reactions of 4-hydroxycoumarin and substituted 4-hydroxycoumarin with various terminal alkynes have been studied. In case of internal alkyne (prop-1-yn-1-ylbenzene), the reaction with 4-hydroxycoumarin led to the corresponding product with an E/Z ratio of 3:1. This protocol is operationally very simple and has much potential for the synthesis of heteroarylated vinyl ethers from basic chemicals.

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Indium(III) Catalyzed Direct sp3-sp C-C Bond Formation from Alcohols and Terminal Alkynes

Letters in Organic Chemistry ◽

10.2174/1570178611310080004 ◽

2013 ◽

Vol 10 (8) ◽

pp. 555-561 ◽

Cited By ~ 5

Author(s):

Guangming Nan ◽

Jun Zhou

Keyword(s):

Bond Formation ◽

Terminal Alkynes

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Transition Metal-Catalyzed Carboxylation of Terminal Alkynes with CO2

Mini-Reviews in Organic Chemistry ◽

10.2174/1570193x15666180101150819 ◽

2018 ◽

Vol 15 (4) ◽

pp. 283-290 ◽

Cited By ~ 8

Author(s):

Chang Qiao ◽

Yu Cao ◽

Liang-Nian He

Keyword(s):

Transition Metal ◽

Terminal Alkynes ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Synthesis of Novel 1,2,3-Triazole Derivatives of Isocoumarins and 3,4-Dihydroisocoumarin with Potential Antiplasmodial Activity In Vitro

Medicinal Chemistry ◽

10.2174/1573406416666200602161047 ◽

2020 ◽

Vol 16 ◽

Author(s):

Lucas da Silva Santos ◽

Matheus Fillipe Langanke de Carvalho ◽

Ana Claudia de Souza Pinto ◽

Amanda Luisa da Fonseca ◽

Julio César Dias Lopes ◽

...

Keyword(s):

Triazole Ring ◽

Antiplasmodial Activity ◽

World Health ◽

Dipolar Cycloaddition ◽

Terminal Alkynes ◽

The World ◽

Ic50 Values ◽

Derivatives Of ◽

Active Substances

Background: Malaria greatly affects the world health, having caused more than 228 million cases only in 2018. The emergence of drug resistance is one of the main problems in its treatment, demonstrating the urge for the development of new antimalarial drugs. Objective: Synthesis and in vitro antiplasmodial evaluation of triazole compounds derived from isocoumarins and a 3,4- dihydroisocoumarin. Method: The compounds were synthesized in 4 to 6-step reactions with the formation of the triazole ring via the Copper(I)-catalyzed 1,3-dipolar cycloaddition between isocoumarin or 3,4-dihydroisocoumarin azides and terminal alkynes. This key reaction provided compounds with an unprecedented connection of isocoumarin or 3,4-dihydroisocoumarin and the 1,2,3-triazole ring. The products were tested for their antiplasmodial activity against a Plasmodium falciparum chloroquine resistant and sensitive strains (W2 and 3D7, respectively). Results: Thirty-one substances were efficiently obtained by the proposed routes with an overall yield of 25-53%. The active substances in the antiplasmodial test displayed IC50 values ranging from 0.68-2.89 μM and 0.85-2.07 μM against W2 and 3D7 strains, respectively.

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