Skip to main content
SpringerLink
Log in

Mild and Efficient Synthesis of Polysubstituted Phthalimides and Piperidines Catalyzed by DABCO

  • Research Paper
  • Published:
Iranian Journal of Science and Technology, Transactions A: Science Aims and scope Submit manuscript

Abstract

Polysubstituted phthalimide derivatives have been isolated in excellent yield from the addition reaction between acetoacetanilide and dialkyl acetylenedicarboxylates by using DABCO as an efficient basic catalyst in EtOH at room temperature. This procedure led to the formation of new phthalimide derivative in the presence of di-tert-butylacetylendicarboxylate as acetylenic ester. The methodology has also been applied successfully for the synthesis of novel piperidine substitutes via the simple reaction between acetoacetanilide and alkyl propiolates. These reactions have some advantages such as not only the process is eco-friendly but also the yields are good and the work-up is simple.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Barhoumi-Slimi TM, Ourévitch M (2018) β-chloro-α, β-unsaturated carbonyls as convenient precursors of highly substituted benzenes. J Iran Chem Soc 15(3):629–636

    Article  Google Scholar 

  • Buncel E, Dust JM, Terrier F (1995) Rationalizing the regioselectivity in polynitroarene anionic. sigma.-adduct formation. Relevance to nucleophilic aromatic substitution. Chem Rev 95(7):2261–2280

    Article  Google Scholar 

  • Carballo RM, Ramirez MA, Rodríguez ML, Martin VS, Padrón JI (2006) Iron (III)-promoted aza-Prins-cyclization: direct synthesis of six-membered azacycles. Org Lett 8(17):3837–3840

    Article  Google Scholar 

  • Daly JW, Spande TF, Garraffo HM (2005) Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds. J Nat Prod 68(10):1556–1575

    Article  Google Scholar 

  • Dastoorani P, Maghsoodlou MT, Khalilzadeh MA, Sarina E (2016) Synthesis of new dibenzofuran derivatives via Diels–Alder reaction of euparin with activated acetylenicesters. Tetrahedron Lett 57(3):314–316

    Article  Google Scholar 

  • Davis FA, Chao B, Rao A (2001) Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer. Org Lett 3(20):3169–3171

    Article  Google Scholar 

  • Fustero S, Jiménez D, Moscardó J, Catalán S, del Pozo C (2007) Enantioselectiveorganocatalytic intramolecular aza-Michael reaction: a concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine. Org Lett 9(25):5283–5286

    Article  Google Scholar 

  • Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Aryl − aryl bond formation one century after the discovery of the Ullmann reaction. Chem Rev 102(5):1359–1470

    Article  Google Scholar 

  • Ho B, Crider AM, Stables JP (2001) Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores. Eur J Med Chem 36(3):265–286

    Article  Google Scholar 

  • Jazinizadeh T, Maghsoodlou MT, Heydari R, Yazdani-Elah-Abadi A (2017) Na2EDTA: an efficient, green and reusable catalyst for the synthesis of biologically important spirooxindoles, spiroacenaphthylenes and spiro-2-amino-4H-pyrans under solvent-free conditions. J Iran Chem Soc 14(10):2117–2125

    Article  Google Scholar 

  • Lebold TP, Leduc AB, Kerr MA (2009) Zn (II)-catalyzed synthesis of piperidines from propargyl amines and cyclopropanes. Org Lett 11(16):3770–3772

    Article  Google Scholar 

  • Mali AS, Potnis CS, Chaturbhuj GU (2018) Aluminized polyborate: a novel catalyst for the multicomponent solvent-free synthesis of alkyl 1, 2, 6-trisubstituted-4-[(hetero) arylamino]-1, 2, 5, 6-tetrahydropyridine-3-carboxylates. J Iran Chem Soc 15(6):1399–1409

    Article  Google Scholar 

  • Misra M, Pandey SK, Pandey VP, Pandey J, Tripathi R, Tripathi RP (2009) Organocatalyzed highly atom economic one pot synthesis of tetrahydropyridines as antimalarials. Bioorg Med Chem 17(2):625–633

    Article  Google Scholar 

  • Mohebat R, Yazdani-Elah-Abadi A, Maghsoodlou MT, Hazeri N (2017) DABCO-catalyzed multi-component domino reactions for green and efficient synthesis of novel 3-oxo-3H-benzo[a]pyrano[2,3-c]phenazine-1-carboxylate and 3-(5-hydroxybenzo[a]phenazin-6-yl) acrylate derivatives in water. Chin Chem Lett 28(5):943–948

    Article  Google Scholar 

  • Murty MS, Ram KR, Yadav JS (2008) BiCl3 promoted aza-Prins type cyclization: a rapid and efficient synthesis of 2, 4-disubstituted piperidines. Tetrahedron Lett 49(7):1141–1145

    Article  Google Scholar 

  • O’Hagan D (2000) Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids. Nat Prod Rep 17(5):435–446

    Article  Google Scholar 

  • Pearson DE, Buehler CA (1972) Friedel–Crafts acylations with little or no catalyst. Synthesis 10:533–542

    Google Scholar 

  • Petit S, Nallet JP, Guillard M, Dreux J, Chermat R, Poncelet M, Bulach C, Simon P, Fontaine C, Barthelmebs M, Imbs JL (1991) Synthesis and psychotropic activity of 3,4-diarylpiperidines: structure-activity relationship and antihypertensive activity antihypertensive. Eur J Med Chem 26(1):19–32

    Article  Google Scholar 

  • Saito S, Yamamoto Y (2000) Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives. Chem Rev 100(8):2901–2916

    Article  Google Scholar 

  • Sajadikhah SS, Hazeri N, Maghsoodlou MT, Habibi-Khorassani SM, Beigbabaei A, Willis AC (2013) Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles. J Iran Chem Soc 10(5):863–871

    Article  Google Scholar 

  • Sales M, Charette AB (2005) A Diels–Alder approach to the stereoselective synthesis of 2, 3, 5, 6-tetra-and 2, 3, 4, 5, 6-pentasubstituted piperidines. Org Lett 7(26):5773–5776

    Article  Google Scholar 

  • Samai S, Ghosh D, Das UK, Atta S, Manna SK, Maiti DK (2016) Water–the best solvent for DMAP-mediated dual cyclization towards metal-free first synthesis of fully substituted phthalimides. Green Chem 18(10):2961–2965

    Article  Google Scholar 

  • Sharghi H, Aberi M, Doroodmand MM, Shiri P (2017) Chromium (III)-salen complex nanoparticles on AlPO4: as an efficient heterogeneous and reusable nanocatalyst for mild synthesis of highly functionalized piperidines, 2-arylbenzimidazoles, and 2-arylbenzothiazoles. J Iran Chem Soc 14(7):1557–1573

    Article  Google Scholar 

  • Sharghi H, Aboonajmi J, Aberi M, Shiri P (2018) Heterogeneous AlPO4(SO3H) nanosheets: novel catalyst for the multi-component synthesis of quinazolinones and highly functionalized piperidines. J Iran Chem Soc 15(5):1107–1118

    Article  Google Scholar 

  • Sheldrick GM (1990) Phase annealing in SHELX-90: direct methods for larger structures. Actacrystallogr A 46(6):467–473

    Article  Google Scholar 

  • Smith MB (2001) J. March in advanced organic chemistry. Wiley, New York

    Google Scholar 

  • Snieckus V (1990) Directed orthometalation: tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics. Chem Rev 90(6):879–933

    Article  Google Scholar 

  • Takasu K, Shindoh N, Tokuyama H, Ihara M (2006) Catalytic imino Diels–Alder reaction by triflic imide and its application to one-pot synthesis from three components. Tetrahedron 62(51):11900–11907

    Article  Google Scholar 

  • Trost BM (1991) The atom economy: a search for synthetic efficiency. Science 254(5037):1471–1477

    Article  Google Scholar 

  • Zhou Y, Gregor VE, Ayida BK, Winters GC, Sun Z, Murphy D, Haley G, Bailey D, Froelich JM, Fish S, Webber SE, Hermann T, Wall D (2007) Synthesis and SAR of 3, 5-diamino-piperidine derivatives: novel antibacterial translation inhibitors as aminoglycoside mimetics. Bioorg Med Chem Lett 17(5):1206–1210

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan

Author information

Authors and Affiliations

  1. Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    Farideh Paymozd, Malek-Taher Maghsoodlou, Reza Heydari & Mehrnoush Kangani

  2. Department of Chemistry, Payame Noor University, Tehran, 19395-3697, Iran

    Afshin Yazdani-Elah-Abadi

  3. Research Center of Environmental Chemistry, Payame Noor University, Ardakan, Yazd, Iran

    Afshin Yazdani-Elah-Abadi

  4. Department of Biology, Science and Arts University, Yazd, Iran

    Afshin Yazdani-Elah-Abadi

  5. Department of Chemistry, Università degli Studi di Parma, Parma, Italy

    Claudia Graiff

Authors
  1. Farideh Paymozd
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Malek-Taher Maghsoodlou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Reza Heydari
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Afshin Yazdani-Elah-Abadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mehrnoush Kangani
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Claudia Graiff
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Malek-Taher Maghsoodlou.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Paymozd, F., Maghsoodlou, MT., Heydari, R. et al. Mild and Efficient Synthesis of Polysubstituted Phthalimides and Piperidines Catalyzed by DABCO. Iran J Sci Technol Trans Sci 43, 2851–2859 (2019). https://doi.org/10.1007/s40995-019-00789-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40995-019-00789-z

Keywords

Search

Navigation