Microwave-Enhanced One-Pot Synthesis of Diversified 3-Acyl-5-Hydroxybenzofurans

Cheng, Xiamin; Liu, Xuewei

doi:10.1021/cc070015u

Cited by 41 publications

(9 citation statements)

References 15 publications

(17 reference statements)

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“…Another method that has been used to synthesize benzoylbenzofurans devoid of substituents at C-2 is the conjugate addition of enaminoketones to 1,4-benzoquinones. The latter method was employed in this study because it utilizes readily available starting acetophenones and benzoquinones and also affords the 3-benzoylbenzofurans in a few steps and in good yields. − As shown in Scheme , the synthesis was initiated by reacting the TBDMS-protected acetophenone 8 with N,N -dimethylformamide dimethylacetal (DMF–DMA) followed by benzoquinone in HOAc. This gave the benzoylbenzofuran 9 in a low yield and the chromone 11 in a high yield .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Isoflavones by Tandem Demethylation and Ring-Opening/Cyclization of Methoxybenzoylbenzofurans

2019

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The unexpected conversion of benzoylbenzofurans into isoflavones through an intramolecular cascade that involves deprotection and ring-opening/cyclization is described. This was discovered in an investigation of the possible transformation of benzoylbenzofurans into coumaronochromones. This route affords isoflavones in two major steps from acetophenones and benzoquinones. The transformation was validated by synthesizing differently substituted isoflavone derivatives and further applied to a concise synthesis of a potential anticancer lead compound, glaziovianin A (1).

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Section: Resultsmentioning

confidence: 99%

Synthesis of Isoflavones by Tandem Demethylation and Ring-Opening/Cyclization of Methoxybenzoylbenzofurans

2019

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“…On the other hand, the reactions of enaminones of type 1 with quinones were known to provide 5‐hydroxybenzofurans, wherein the attack of the O‐nucleophilic site to the C–N bond in tertiary enaminones allowed the benzofuran annulations. After the primary investigation of Elnagdi et al,44 Liu and co‐worker45 reported their systematic work on the microwave‐assisted synthesis of the hydroxybenzofurans 87 via the reactions of tertiary enaminones and benzoquinones 86 (Scheme ).…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines

Wan

Gao

2016

The Chemical Record

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Electron-deficient enamines such as enaminones and enaminoesters are moieties showing widespread application in organic synthesis. Among the various available electron-deficient enamines, the N,N-disubstituted amino-functionalized ones (tertiary enamines) represent a class of special enamines with distinct properties and important applications. Based on our longstanding interest in exploring novel synthetic methods using electron-deficient tertiary enamines, we present herein the research advances in organic synthesis via domino reactions making use of the combinatorial C-N, C=C, C-H, and other bond transformations of electron-deficient tertiary enamines.

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“…Microwave irradiation technology in organic synthesis is a powerful tool for drug synthesis as it can speed up the reactions under mild conditions allowing the rapid preparation of compounds. 30 As mentioned above, microwave irradiation technology has been successfully applied to the synthesis of N-arylthieno [2,3-d] 33 by microwave irradiation technology (Figure 4).…”

Section: Introductionmentioning

confidence: 99%

A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl‑5,6,7,8‑tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amines

Han¹,

Yin²,

Sui³

et al. 2019

J. Braz. Chem. Soc.

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A series of N-aryl-5,6,7,8-tetra-hydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amines were synthesized in moderate to good yield by using a microwave-enhanced conditions. The selected compounds were evaluated for their cytotoxic effects (IC 50 values) on human pulmonary carcinoma (A549), murine BALB/c spontaneous colon adenocarcinoma (CT26) and human hepatocellular liver carcinoma (HepG2) cell lines in vitro. Amongst these compounds, one compound was found to have the better cytotoxic activity with reference to the standard Erlotinib hydrochloride (Tarceva TM) against A549 (IC 50 = 16.06 ± 0.09 μM) and HepG2 (IC 50 = 15.01 ± 0.31 μM) cell lines. Especially, two compounds showed best cytotoxic effects against CT26 (IC 50 = 11.38 ± 0.44 μM) and HepG2 (IC 50 = 8.51 ± 0.52 μM) cell lines, respectively. The preliminary structure-activity relationships were disclosed and the thieno[2,3-d]pyrimidine skeleton could be exploited to potential antitumor agents in the future.

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Microwave-Enhanced One-Pot Synthesis of Diversified 3-Acyl-5-Hydroxybenzofurans

Cited by 41 publications

References 15 publications

Synthesis of Isoflavones by Tandem Demethylation and Ring-Opening/Cyclization of Methoxybenzoylbenzofurans

Synthesis of Isoflavones by Tandem Demethylation and Ring-Opening/Cyclization of Methoxybenzoylbenzofurans

Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines

A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl‑5,6,7,8‑tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amines

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