New DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) Assisted One-Pot Synthesis of 2,8-Disubstituted 4H-1-Benzopyran-4-ones

Riva, Carlo Ruga; Toma, Carlo De; Donadel, Leandro; Boi, C.; Pennini, R.; Motta, G; Leonardi, Amedeo

doi:10.1055/s-1997-1168

Cited by 43 publications

(13 citation statements)

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“…The one pot cyclization reaction was developed from the method of Riva et al [14]. The phenolic ester intermediate was initially formed from the reaction of phenolic ketone and acid chloride.…”

Section: Chemical Synthesismentioning

confidence: 99%

Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

Ungwitayatorn

Wiwat

Samee

et al. 2011

Journal of Molecular Structure

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Section: Chemical Synthesismentioning

confidence: 99%

Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

Ungwitayatorn

Wiwat

Samee

et al. 2011

Journal of Molecular Structure

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“…Treatment of (±)-15 with Ac 2 O and DBU in pyridine heated at 60°C produced (±)-16 in 53 % yield. [15] The reduction of the lactone moiety in (±)-16 with DIBAL in CH 2 Cl 2 afforded (±)-2, which is the proposed structure of aspergione B. The 1 H-and 13 C NMR spectroscopic data of our synthetic (±)-2 were different from those of natural 2 reported by Proksch et al (Table 1).…”

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confidence: 52%

Synthesis and Absolute Configuration of (+)‐Pseudodeflectusin: Structural Revision of Aspergione B

et al. 2006

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We report herein the total synthesis and determination of the absolute configuration of (+)‐pseudodeflectusin. The total synthesis of (+)‐pseudodeflectusin starting from o‐anisic aid was achieved in 11 total steps with an overall yield of 2.0 %. The 1H‐ and 13C NMR spectroscopic data of our synthetic pseudodeflectusin was identical to that of the natural compound. The absolute configuration of (+)‐pseudodeflectusin was determined by chiral HPLC and X‐ray crystallographic analyses. We also synthesized the proposed structure of aspergione B, whose 1H‐ and 13C NMR spectroscopic data is identical to that of pseudodeflectusin. The 1H‐ and 13C NMR spectra of our synthetic aspergione B were different from those of the natural compound reported by Proksch et al. Our results confirm that aspergione B and pseudodeflectusin are, in fact, the same compound.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…Treatment with KOtBu in DMF at 60 8C induced a Baker-Venkataraman rearrangement [18][19][20] in combination with the cleavage of the methyl ether to give the 1,3-diketone 15.…”

Section: Chemistrymentioning

confidence: 99%

“…[21] The resulting benzyl amine 19 could by converted into the b-diketone 21 upon reaction with 2-hydroxyacetophenone (1). Starting from methyl 4-indolecarboxylate (20), Claisen condensation yielded the corresponding 1,3-diketone 22.…”

Section: Chemistrymentioning

confidence: 99%

Diarylpropane‐1,3‐dione Derivatives as TetR‐Inducing Tetracycline Mimetics: Synthesis and Biological Investigations

Kormann¹,

Pimenta²,

Löber³

et al. 2009

ChemBioChem

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Synthesis, biological investigations and molecular docking studies of nonantibiotic and nontetracyclic inducers that feature a minimal key motif of the natural lead tetracycline are presented. The diarylpropane-1,3-dione motif was identified as the minimal substructure responsible for TetR induction by tetracyclines. The first nontetracyclic surrogates of the natural tetracyclines displayed significant inducing effects for TetR(BD)S135L, whereby the chlorohydroxyphenyl-substituted beta-diketone 31 displayed the highest activity. Interestingly, antibiotic activity could not be detected for 31. Homology modeling based on the X-ray structure of 7-chlorotetracycline bound to TetR indicated analogous binding modes for the natural inducer and the synthetic diarylpropane-1,3-dione derivatives.

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New DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) Assisted One-Pot Synthesis of 2,8-Disubstituted 4H-1-Benzopyran-4-ones

Cited by 43 publications

References 0 publications

Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

Synthesis and Absolute Configuration of (+)‐Pseudodeflectusin: Structural Revision of Aspergione B

Diarylpropane‐1,3‐dione Derivatives as TetR‐Inducing Tetracycline Mimetics: Synthesis and Biological Investigations

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