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Ph3P-mediated synthesis of fused 1,2-dihydropyridines

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Abstract

The zwitterionic intermediates, generated in situ from Ph3P and dialkyl acetylenedicarboxylates, are trapped by N–H acidic 2-(alkylamino)-2-(1,3-dioxo-1H-inden-2(3H)-ylidene)acetonitriles in refluxing toluene to afford dialkyl 2-alkyl-1-cyano-9-oxo-3,9-dihydro-2H-indeno[2,1-c]pyridine-3,4-dicarboxylates in good yields. The structure of a typical product was confirmed by X-ray crystallography.

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Acknowledgements

We thank the Research Council of Tarbiat Modares University for supporting this work.

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Correspondence to Issa Yavari.

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Yavari, I., Safaei, M. & Abbasi, A. Ph3P-mediated synthesis of fused 1,2-dihydropyridines. Monatsh Chem 151, 107–112 (2020) doi:10.1007/s00706-019-02530-3

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Keywords

  • 1,2-Dihydropyridines
  • Acetylenic esters
  • Intramolecular Wittig reaction
  • Alkylamines
  • Ninhydrin