A conventional BF 3 ·OEt 2 -mediated Bradsher-type cyclodehydration of 2-arylmethyl benzaldehydes in CH 2 Cl 2 at room temperature gave polycyclic aromatic and heteroaromatic compounds. Alternatively, these compounds could be syn-
One pot syntheses of substituted dibenzothiophene S,S-dioxides and fluorenones were successfully achieved by Diels-Alder reaction of benzo[c]furans with thiophene S,S-dioxides and indenones, respectively. Photophysical properties of representative seven- and nine-membered dibenzothiophene S,S-dioxide acenes were also reported.
1,3-Diarylisobenzofuran-DMAD adducts upon reaction with BF3·OEt2 in DCM at room temperature underwent a regiospecific 1,2-aryl migration followed by the Krapcho decarboxylation to give tri-substituted α-naphthols in good yields.
Diels-Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence...
Diels-Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4-diaryl substituted naphthalenes, fluoranthenes, and fluorenones. The photophysical properties of representative diaryl-substituted hydrocarbons are also reported.
A straightforward and general method for the synthesis of annulated thiophene, dibenzothiophene, and carbazoles analogues has been achieved involving alkylation of 2-bromo-1-(phenylsulfonylmethyl)arene/heteroarene with arylmethyl bromides/heteroarylmethyl bromides using t-BuOK as a base in DMF, followed by Pd(0)-mediated intramolecular Heck coupling in the presence of KCO in DMF at 80-140 °C. The attractive feature of this protocol is that a wide variety of π-conjugated heterocycles could be readily accessed by an appropriate choice of arylmethylsulfones and benzylic bromides.
Diels–Alder reaction of symmetrical/unsymmetrical benzo[c]furans with acenaphthylene in xylenes at reflux temperatures followed by p‐toluenesulfonic acid‐mediated epoxide cleavage and dehydration furnished diaryl/heteroaryl‐substituted benzo[k]fluoranthenes. This strategy could be successfully applied to the synthesis of dimeric and trimeric benzo[k]fluoranthenes. Functionalization of representative benzo[k]fluoranthene derivatives was also performed. UV/Visible, emission and electrochemical properties of representative fluoranthene derivatives are also reported.
A new series of 3,4‐ethylenedioxythiophene (EDOT)‐appended propenones were prepared by condensation reaction and their in vitro cytotoxicity effects were evaluated against five human cancer cell lines. Preliminary structure–activity relationships of EDOT‐incorporated 2‐propenone derivatives were also established. The EDOT‐appended enones demonstrated significant cytotoxicity against human cancer cell lines. The most active analogue, (E)‐3‐(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)‐1‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one (3 p, GI50=110 nm), severely inhibited the clonogenic potential of cancer cells, and induced cell‐cycle arrest in the G2/M phase and caused an accumulation of HCT116 colon cancer cells with >4 N DNA content. Also, 3 p exhibited weak inhibition of the enzymatic activity of human topoisomerase I. Molecular docking studies indicated preferential binding of the compounds to the ATP‐binding pocket of the human checkpoint 2 kinase (Chk2) catalytic domain, thus, identifying a novel diaryl 2‐propenone chemotype for the development of potent inhibitors of Chk2.
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