Reactions of the Hydrofluoroborate Salts of Open-Chain Analogues of Reissert Compounds with Some α,β-Ethylenic Esters

Perrin, Sandrine; Monnier, K.; Laude, B.; Kubicki, Marek M.; Blacque, Olivier

doi:10.1002/(sici)1099-0690(199901)1999:1<297::aid-ejoc297>3.0.co;2-j

Cited by 15 publications

(4 citation statements)

References 19 publications

(7 reference statements)

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“…These data, combined with HSQC and HMBC studies, confirmed the formation of a dicationic allylic isoxazolium ring (Scheme 4), often referred to as a Reissert salt. [25][26][27] Addition of DABCO to 13 results in the isolation of compound 14, a tautomer of 4. Returning a sample of 14 to an acidic acetonitrile solution quantitatively regenerated allyl 13.…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR (CDCl 3 , δ): major, 5.69-5.86 (m, 2H, H4/H5), 4.09 (ddd, J ) 19.3, 2.5, 2.4, 1H, H6), 3.97 (ddd, J ) 19.3, 2.6, 2.4, 1H, H6′), 3.76 (s(shoulder), 3H, Ester-Me(maj,min)), 3.75 (s, 3H, Ester-Me′), 3.63 (dd, J ) 13.8, 4.3, 1H, H2), 3.53 (dd, J ) 13.8, 5.5, 1H, H2′), 3.40 (d, J ) 9.4, 1H, H7), 3.03 (s(broad), 1H, H3), 2.09 (s, 3H, Amide-Me); minor, 5. 69 (27). Acetone (4.17 g) was added to a vial containing 22 (0.102 g, 0.135 mmol) and I 2 (0.207 g, 0.816 mmol), and the dark brown solution was allowed to stir.…”

Section: [Tpw(no)(pme 3 )(45-η 2 -(1-acetyl-2-cyanopiperidin-4-ylium)...mentioning

confidence: 99%

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Polarization of the Pyridine Ring: Highly Functionalized Piperidines from Tungsten−Pyridine Complex

et al. 2010

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The N-acetylpyridinium complex of {TpW(NO)(PMe3)} undergoes regio- and stereoselective reactions with a broad range of common organic nucleophiles, providing a family of 1,2-dihydropyridine (DHP) complexes of the form TpW(NO)(PMe3)(3,4-η(2)-DHP). The present study explores the elaboration of these systems into novel piperidines. The addition of an acid to the DHP complexes generates highly asymmetric π-allyl complexes that in turn react with a second nucleophile at either C3 or C5. The subsequent oxidative decomplexation of these materials yields several piperidinamides with unconventional substitution patterns.

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Section: Resultsmentioning

confidence: 99%

Section: [Tpw(no)(pme 3 )(45-η 2 -(1-acetyl-2-cyanopiperidin-4-ylium)...mentioning

confidence: 99%

Polarization of the Pyridine Ring: Highly Functionalized Piperidines from Tungsten−Pyridine Complex

et al. 2010

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“…Monnier-Jobé and col. describe the synthesis of ethyl-3,6-diphenyl-2-1H-pyridone-4-carboxylate by 1,3-dipolar cycloaddition from mesoionic species and an acrylate ester [79]. Monnier-Jobé and col. describe the synthesis of ethyl-3,6-diphenyl-2-1H-pyridone-4-carboxylate by 1,3-dipolar cycloaddition from mesoionic species and an acrylate ester [79].…”

Section: From Other Aromatic Heterocyclic Ringsmentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

202

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The synthesis of a substituted 2-pyridone ring is a topical area of continuing interest due to the number of biologically active molecules containing this moiety. Over the last decade, natural compounds with this structure have emerged as potent antitumor antiviral and attention, because those compounds may be studied as a simple model for investigating mechanisms of some enzymatic reactions or for discerning the behavior of nucleic acids bases in connection with mutation due to base mispairing or other mistaken helices. Recent studies have shown the usefulness of 2-pyridones as intermolecular connectors between building blocks in material science. Thus, despite the large number of methods known for their synthesis, new procedures are continuously being developed. Two main synthetic approaches can be found in the literature: from other heterocycles systems or condensation of acyclic systems. The latter can be further classified depending on the bond formed in the cyclization step: by C-C or C-N bond generation. The latter can be subclassified depending on the first condensation step. This is a review of new or improved methods for constructing 2-pyridone rings. This article will be restricted to ring formation, which can be included in the total synthesis of several compounds with specific biological or material properties.The pursuit of these properties requires efficient synthetic routes that allow rapid assembly and variation of multiple pendant substituents on the heteroaromatic case, which permits rapid analogsynthesis (RAS) [1].

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“…[1][2][3][4][5][6][7][8][9] Therefore there are numerous known methods for their synthesis [10][11] and new procedures are continually being developed. [12][13][14][15][16][17] Our previous studies 29,30 on the reactivity of an open-chain analogue of Reissert compound hydrofluoroborate salt 1aA (Ar 1 = Ar 2 = Ph) with ethyl acrylate have led us to the synthesis of ethyl 3,6-diphenyl-2-1H-pyridone-4-carboxylate 6aAE (Ar 1 = Ar 2 = Ph, R = Et) (Scheme 1). The structural advantage and the convenient synthetic method of this compound led us to look for the generalisation of this procedure and we report here a more complete study of the scope of the process.…”

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confidence: 99%