The effect of thiophene ring substitution position on the properties and electrochemical behaviour of alkyne–dicobaltcarbonylthiophene complexes

Arnanz, Avelina; Marcos, M.L.; Delgado, Salomé; González‐Velasco, J.; Moreno, C.

doi:10.1016/j.jorganchem.2008.08.005

Cited by 19 publications

(19 citation statements)

References 87 publications

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“…Magnus reported that the less sterically encumbered alkynyl moiety preferentially complexes to [Co 2 (CO) 8 ] . Later, Arnanz et al established that the less electron‐enriched triple bond at the 2‐position of the thiophene ring favors complexation, because of the extra stabilization of the complexes by enhanced back‐donation from the Co d orbitals to the π* MO of the triple bond . It is clear that for enediynes 9a , b and 15a , b , the steric factor is not important and it is mainly the electronic effects of both the benzothiophene and the O‐containing substituents that should be taken into account.…”

Section: Resultsmentioning

confidence: 99%

Oxaenediynes through the Nicholas‐Type Macrocyclization Approach

et al. 2016

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The Nicholas‐type macrocyclization has been used for the first time for the synthesis of 10‐ and 11‐membered oxaenediynes fused to a benzothiophene. The acyclic starting materials were easily synthesized by electrophilic cyclization of o‐(buta‐1,3‐diynyl)thioanisoles followed by a Sonogashira coupling of the resulting 2‐ethynyl‐3‐iodobenzothiophenes with functionalized alkynes. A high reactivity of the 10‐membered oxacycles in the Bergman cyclization was predicted by DFT calculations and confirmed by differential scanning calorimetry. The ability of enediynes to induce single‐strand PM2 DNA scissions was also found.

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Section: Resultsmentioning

confidence: 99%

Oxaenediynes through the Nicholas‐Type Macrocyclization Approach

et al. 2016

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“…Complexation of acyclic enediyne 9 with octacarbonyl dicobalt proceeded smoothly upon less electron-enriched C2 triple bond. 44,53,54 The Nicholas cyclization of the complex 10 obtained was carried out under common conditions for the Nicholas reaction.…”

Section: Letter Syn Lettmentioning

confidence: 99%

10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability

Danilkina¹,

Rumyantsev²,

Lyapunova³

et al. 2018

Synlett

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The Nicholas-type macrocyclization through NH-tosyl functional group has been found to be an efficient technique for the synthesis of a 10-membered azaenediyne system annulated with a benzothiophene. To compare the activity of azaenediyne synthesized with similar oxa- and carbocyclic enediynes the Bergman cyclization activation energies and the ability of enediynes to cleave DNA (pBR322 plasmid) were investigated. The order of reactivity predicted by DFT calculations (N-enediyne < C-enediyne < O-enediyne) was confirmed by DSC analysis data. Surprisingly azaenediyne was found to be more active in the DNA cleavage assay than the C-analogue.

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“…Initially, ((3‐bromothiophen‐2‐yl)ethynyl)trimethylsilane 2 was prepared from the reaction between 2,3‐dibromothiophene 1 and trimethylsilylacetylene by using Pd‐catalyzed Sonogashira cross coupling reaction (65% yield) (Scheme ). Then, we focused on the synthesis of 2‐ethynyl‐3‐(aryl/alkyl‐ethynyl)thiophene derivatives 4 as a starting compound for the formation of designed thieno[2,3‐ a ]dibenzothiophenes 8 .…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and In vitro Evaluation of Thieno[a]dibenzothiophene Derivatives

et al. 2020

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A variety of highly substituted thieno[2,3‐a]dibenzothiophenes and thieno[3,2‐a]dibenzothiophenes are readily prepared via cascade electrophilic cyclization reaction. The reaction was tolerated a variety of compounds. In the present study, antimicrobial and antifungal activities were investigated for all synthesized molecules against A. niger ATCC 16404, C. albicans ATCC 10231, S. aureus ATCC 25923 and B. subtilis ATCC 6633, respectively.

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The effect of thiophene ring substitution position on the properties and electrochemical behaviour of alkyne–dicobaltcarbonylthiophene complexes

Cited by 19 publications

References 87 publications

Oxaenediynes through the Nicholas‐Type Macrocyclization Approach

Oxaenediynes through the Nicholas‐Type Macrocyclization Approach

10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability

Design, Synthesis, and In vitro Evaluation of Thieno[a]dibenzothiophene Derivatives

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