Ph3P-mediated synthesis of fused 1,2-dihydropyridines

  • 48 Accesses


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.

Graphic abstract

This is a preview of subscription content, log in to check access.

Access options

Buy single article

Instant unlimited access to the full article PDF.

US$ 39.95

Price includes VAT for USA

Subscribe to journal

Immediate online access to all issues from 2019. Subscription will auto renew annually.

US$ 199

This is the net price. Taxes to be calculated in checkout.


  1. 1.

    Sharma VK, Singh SK (2017) RSC Adv 7:2682

  2. 2.

    Martin RM, Bergman RG, Ellman JA (2013) Org Lett 15:444

  3. 3.

    Berti F, Bussolo VD, Pineschi M (2013) J Org Chem 78:7324

  4. 4.

    Hantzsch A (1882) Liebigs Ann Chem 215:1

  5. 5.

    Stout DM, Meyers AI (1982) Chem Rev 82:223

  6. 6.

    Wan J-P, Liu Y (2012) RSC Adv 2:9763

  7. 7.

    Silva EMP, Varandas PAMM, Silva AMS (2013) Synthesis 2013:3053

  8. 8.

    Bull JA, Mousseau JJ, Pelletier G, Charette AB (2012) Chem Rev 112:2642

  9. 9.

    Tanaka K, Mori H, Yamamoto M, Katsumura S (2011) J Org Chem 66:3099

  10. 10.

    Sklenicka HM, Hsung RP, Wei L-L, McLaughlin MJ, Gerasyuto AL, Degen SJ (2000) Org Lett 2:1161

  11. 11.

    Cao S, Xin L, Liu Y, Wan J-P, Wen C (2015) RSC Adv 5:27372

  12. 12.

    Yavari I, Bayat MJ, Sirouspour M, Souri S (2010) Tetrahedron 66:7995

  13. 13.

    Resende DISP, Guieu S, Oliva CG, Silva AMS (2014) Tetrahedron Lett 55:585

  14. 14.

    Hoshimoto Y, Ohata T, Ohashi M, Ogoshi S (2014) Chem Eur J 20:4105

  15. 15.

    Zou G-F, Hu Z-P, Zhang S-Q, Liao W-W (2015) Tetrahedron Lett 56:937

  16. 16.

    Trost BM, Biannic B (2015) Org Lett 17:1433

  17. 17.

    Guo H, Fan YC, Sun Z, Wu Y, Kwon O (2018) Chem Rev 118:10049

  18. 18.

    Amatore M, Lebœuf D, Malacria M, Gandon V, Aubert A (2013) J Am Chem Soc 135:4576

  19. 19.

    Zhang J, Zhang Q, Ji X, Meng L-G (2019) Synlett 30:1095

  20. 20.

    Wang L, Sun M, Ding M-W (2017) Eur J Org Chem 2017:2568

  21. 21.

    Grigg R, Mongkolaussavaratana T (1988) J Chem Soc Perkin Trans 1(1988):541

Download references


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

Author information

Correspondence to Issa Yavari.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2214 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

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

Download citation


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