Skip to main content
Log in

Room Temperature Catalytic Aromatization of Hantzsch 1,4-Dihydropyridines by Sodium Nitrite in the Presence of Acidic Silica Gel

  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

Various alkyl, aryl, and heterocyclic Hantzsch 1,4-dihydropyridines were converted to the corresponding pyridines in excellent yields and short times using sodium nitrite in the presence of a catalytic amount of acidic silica gel at room temperature.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • U Eisner J Kuthan (1972) Chem Rev 72 1 Occurrence Handle10.1021/cr60275a001 Occurrence Handle1:CAS:528:DyaE38Xnt1ehsw%3D%3D

    Article  CAS  Google Scholar 

  • RH Böcker FP Guengerich (1986) J Med Chem 29 1596

    Google Scholar 

  • J Vanden Eynde R D’Orazio YV Havebeke (1994) Tetrahedron 50 2479 Occurrence Handle1:CAS:528:DyaK2cXisVCmuro%3D

    CAS  Google Scholar 

  • Pfister JR (1990) Synthesis 689

  • J Arguello LJ Nunez-Vergara JC Sturm JA Squella (2004) Electrochim Acta 49 4849 Occurrence Handle10.1016/j.electacta.2004.05.037 Occurrence Handle1:CAS:528:DC%2BD2cXms1CnsL4%3D

    Article  CAS  Google Scholar 

  • SH Mashraqui MA Karnik (1998) Tetrahedron Lett 39 4895 Occurrence Handle10.1016/S0040-4039(98)00889-2 Occurrence Handle1:CAS:528:DyaK1cXktlGiu7s%3D

    Article  CAS  Google Scholar 

  • N Nakamichi Y Kawashita M Hayashi (2002) Org Lett 4 3955 Occurrence Handle10.1021/ol0268135 Occurrence Handle1:CAS:528:DC%2BD38XnsVKmtL8%3D

    Article  CAS  Google Scholar 

  • Nakamichi N, Kawashita Y, Hayashi M (2004) Synthesis 1015

  • MM Heravi FK Behbahani HA Oskooie RH Shoar (2005) Tetrahedron Lett 46 2775 Occurrence Handle1:CAS:528:DC%2BD2MXis1eltLk%3D

    CAS  Google Scholar 

  • Han B, Liu Q, Liu Z, Mu R, Zhang W, Liu Z, Yu W (2005) Synlett 2333

  • MM Hashemi Y Ahmadibeni H Ghafuri (2003) Monatsh Chem 134 107 Occurrence Handle1:CAS:528:DC%2BD38XpsFegur8%3D

    CAS  Google Scholar 

  • Dörwald FZ (2002) Organic Synthesis on Solid Phase: Supports, Linkers, Reactions. Wiley-VCH, Weinheim

  • (a) Ho T, Olah GA (1977) J Org Chem 42: 3097; (b) Olah GA, Shih JG, Singh BP (1983) J Org Chem 48: 3356

  • MA Zolfigol M Torabi SE Mallakpour (2001) Tetrahedron 57 8381 Occurrence Handle1:CAS:528:DC%2BD3MXmvFCju70%3D

    CAS  Google Scholar 

  • Y Matsumura Y Yamamoto N Moriyama S Furukubo F Iwasaki O Onomura (2004) Tetrahedron Lett 45 8221 Occurrence Handle1:CAS:528:DC%2BD2cXotFGgur4%3D

    CAS  Google Scholar 

  • (a) Hashemi MM, Ahmadibeni Y (2003) Monatsh Chem 134: 411; (b) Hashemi MM, Akhbari M (2003) Monatsh Chem 134: 1561; (c) Hashemi MM, Karimi-Jaberi Z (2004) Monatsh Chem 135: 41; (d) Hashemi MM, Ghazanfari D, Karimi-Jaberi Z (2004) Monatsh Chem 135: 185; (e) Hashemi MM, Ghazanfari D, Akhbari M (2004) Monatsh Chem 135: 793; (f) Hashemi MM, Ghazanfari D, Ahmadibeni Y, Karimi-Jaberi Z, Ezabadi A (2005) Synth Commun 35: 1103; (g) Hashemi MM, Ezabadi A, Karimi-Jaberi Z (2005) Lett Org Chem 2: 559; (h) Hashemi MM, Eftekhari-Sis B, Khalili B, Karimi-Jaberi Z (2005) J Braz Chem Soc 16: 1082

  • A Hantzsch (1882) Liebigs Ann Chem 1 215

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mohammed M. Hashemi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hashemi, M., Ghafuri, H. & Karimi-Jaberi, Z. Room Temperature Catalytic Aromatization of Hantzsch 1,4-Dihydropyridines by Sodium Nitrite in the Presence of Acidic Silica Gel. Monatsh. Chem. 137, 197–200 (2006). https://doi.org/10.1007/s00706-005-0425-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-005-0425-5

Navigation