En Route to 2-(Cyclobuten-1-yl)-3-(trifluoromethyl)-1<i>H</i>-indole

Gazvoda, Martin; Krivec, Marko; Časar, Zdenko; Košmrlj, Janez

doi:10.1021/acs.joc.8b00100

Cited by 9 publications

(11 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Access to cyclobutenylheteroarenes can be surprisingly difficult. For example, the synthesis of cyclobutenylindole 31 , an impurity in the manufacture of efavirenz ( 32 ), required a major synthetic effort and several of the routes that were tested proved unsuccessful [50] . Efavirenz is an important anti‐HIV/AIDS drug in clinical use, and a high‐quality standard is required for analytical purposes.…”

Section: Figurementioning

confidence: 99%

A Practical Route to Cyclobutanols and Fluorocyclobutanes

Revil-Baudard

Zard

2021

Helvetica Chimica Acta

View full text Add to dashboard Cite

1‐[(Ethoxycarbonothioyl)sulfanyl]cyclobutyl acetate (xanthate 7) was found to add to electronically unbiased alkenes and to certain heteroarenes. In the latter case, this corresponds to a variant of the Minisci reaction and allows the late‐stage modification of biologically active substances. Saponification of the acetate furnishes the corresponding cyclobutanols, which, in the case of the nicotine adduct, can be converted into fluorocyclobutanes by the action of DAST. Fluorocyclobutyl substituted aromatics and heteroaromatics are increasingly present in drug candidates. Heating of the acetoxycyclobutyl derivative of caffeine with TFA gives rise to the cyclobutene analogue. Finally, O‐ethyl S‐[1‐(2,2,2‐trifluoroethoxy)cyclobutyl] carbonodithioate, obtained unexpectedly while optimizing the synthesis of xanthate 7, is a very promising reagent for the introduction of the very rare 2,2,2‐trifluoroethoxycyclobutyl motif.

show abstract

Section: Figurementioning

confidence: 99%

A Practical Route to Cyclobutanols and Fluorocyclobutanes

Revil-Baudard

Zard

2021

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…: 225-227 C. FTIR (KBr, cm À1 ): 3427 (N-H stretch), 1507, 1331 (-NO 2 stretch). 1 Synthesis of 4-(di(1H-Indole-3-yl)methyl)aniline (4). Into a 50-mL two-necked flask, 0.200 g (0.544 mmol) of nitro compound 3, 0.01 g of 10% Pd/C, and 10 mL of ethanol were introduced.…”

Section: Monomer Synthesis Synthesis Of 33 0 -((4-nitrophenyl)methylmentioning

confidence: 99%

“…Indole or 1 H -benzo [b] pyrrole, the heteroaromatic structure alike carbazole, is ever-present in biological and biochemical heterocyclic structure and due to its exceptional chemical, electrical, and optical properties has attracted considerable attention in the fabrication of pharmaceuticals including anticancer, 1 anti-rheumatoidal, 2 antioxidant, 3 anti-HIV, 4 antiproliferative, 5 anti-tubulin, 6 antituberculosis, 7 antibacterial, 8 and anti-inflammatory. 9 The polymers based on indole have been used for the applications in electronics, electrocatalysis, anode materials, anticorrosion coatings, and biological areas.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and properties of highly organosoluble aromatic polyimides containing N-(4-(di(1H-indole-3-yl)methyl)phenyl) moieties

Khalili

Rafiee

2019

High Performance Polymers

View full text Add to dashboard Cite

A new diamine monomer containing indole unit, 3,5-diamino- N-(4-(di(1H-indol-3-yl)methyl)phenyl)benzamide, was successfully synthesized and applied in the preparation of a series of polyimides (PIs) via a conventional two-step polymerization procedure with three aromatic tetracarboxylic dianhydrides. The prepared polymers showed excellent solubility in organic solvents such as N-methyl-2-pyrrolidinone (NMP), N, N-dimethylacetamide, and N, N-dimethylformamide. Flexible and strong films of PIs were obtained via casting from their solutions. The glass transition temperature of these polymers was in the range of 223–264°C. They were fairly stable up to a temperature around 300°C and lost 10% weight at 372°C in nitrogen atmosphere. All of the polymers revealed absorption maxima around 323 nm with a fluorescence emission maxima around 378–406 nm in NMP. The cyclic voltammetry of the PIs exhibited an oxidation wave with a peak at 1.07 V. The resulting polymer films had tensile strengths from 83 MPa to 107 MPa, elongates at break of 7–10%, and tensile moduli of 2.2–2.3 GPa.

show abstract

“…Strained cyclic alkenes are inaccessible hitherto, and a direct route to 2-(cyclobut-1-en-1-yl)-1H-indoles remains unprecedented. 57,58 This is surprising given that 2-(cyclobut-1en-1-yl)-1H-indole analogues and their saturated counterparts have shown promising biological activity, such as the reduction of pain by selective dual iNOS/nNOS inhibition, 59 or anticancer activity by tubulin polymerisation inhibition (Scheme 1b). 60 The use of four-membered ring building blocks in medicinal chemistry remains relatively underdeveloped as chemists depend on a small number of viable protocols towards these moieties.…”

Section: Introductionmentioning

confidence: 99%