Interaction of pentafluorobenzoylpyruvic acid and its esters with N-nucleophiles. Synthesis of 4-oxoquinoline-2-carboxylic acids

Салоутин, В. И.; Skryabina, Z. É.; Basyl, I.T.; Kondrat'ev, P. N.; Чупахин, О. Н.

doi:10.1016/0022-1139(94)03069-3

Cited by 10 publications

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“…It was reported that the reactions of 3-pentafluorinated benzoylpyruvic acid or ester with o-phenylenediamine afforded quinoxalone derivatives. [24][25][26] However, for the reaction of hydroxyl benzoylpyruvic acid with o-phenylenediamine hydrochloride, very recently, the resulting product was reported to be 2-benzimidazole derivatives. 27 Therefore, according to our results, for the first time, we demonstrated authentically that the reaction of benzoylpyruvic acid or ester with o-phenylenediamine or its hydrochloride would give the quinoxalone derivatives, instead of the 2-benzimidazole ones (Scheme 2).…”

Section: Synthesismentioning

confidence: 99%

“…In the present case, formation of compounds 10 or 11 was typical for a reaction of benzoylpyruvate derivatives with aromatic 1,2-dinucleophiles, such as, o-aminophenol and o-phenylenediamine. [24][25][26] Based on the fact that the reaction of methyl benzoylpyruvate with aniline afforded the corresponding enamine at the C2 carbon atom, 24 we speculated that the amino group of the dinucleophilic phenylenediamine might react first with the C-2 electrophilic center to generate the enamine. Then the attack of the second amino group proceeded at the C-1 center to form the six-membered heterocyclic 3,4-dihydroquinoxalone due to thermodynamic factors.…”

Section: Synthesismentioning

confidence: 99%

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Design and Synthesis of p/m‐[p‐(un)Substituted Phenylsulfonamido]phenyl β‐Diketo Acids and Quinoxalone Derivatives

Zeng

Yan

et al. 2007

Chin. J. Chem.

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Diketo acid derivatives are potent and selective HIV-1 integrase inhibitors. To investigate the detailed synthesis of those derivatives, a series of p/m- [p-(un)substituted phenylsulfonamido]phenyl β-diketo acid derivatives have been designed and synthesized. The quinoxalone derivatives as the potential bioisosteres of the biologically labile β-diketoacid pharmacophores have also been synthesized from reactions of the corresponding diketo acids with o-phenylenediamine. The structures of all diketo acid (ester) and quinoxalone derivatives were confirmed by 1 H NMR, 13 C NMR, IR, HRMS and/or MS (ESI). X-ray crystallographic analysis of 11b demonstrates a similar arrangement of the side chain of quinoxalone derivatives with the parent diketoacids due to the intramolecular hydrogen bond (O…H-N) and the sp 2 hybridization configuration of the two nitrogen atoms of the quinoxalone ring.Keywords β-diketo acid, quinoxalone derivative, HIV-1 integrase inhibitor, X-ray crystal structure Figure 1 Structure of diketo acid and designed quinoxalone molecules. β-Diketo acid Chin.goal is to replace the critical diketo acid pharmacophore with quinoxal-2-one moiety.Very recently, we have reported the X-ray crystallographic analysis of 10a, 16 11c 17 and 11d 18 and demonstrated that products from a reaction of 4-(phenylsulfonamido)phenyl-2,4-dioxobutanoic acids with o-phenylenediamine would generate quinoxalone derivatives, rather than 2-substituted benzimidazole derivatives. Here, we present full details of the design and synthesis of a series of p/m- [p-(un)substituted phenylsulfonamido]phenyl β-diketo acid and quinoxalone derivatives. The X-ray crystal structure analysis of a quinoxalone derivative 11b is also disclosed. Scheme 2 The possible products from a reaction of the diketoacid with o-phenylenediamine β-Diketo acid Chin.

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Section: Synthesismentioning

confidence: 99%