Skip to main content
SpringerLink
Log in

Synthesis of polyfunctionalized acrylates via one-pot reactions of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

An efficient synthetic method for the densely substituted 3-arylaminoacrylates was successfully developed via the one-pot reaction of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds such as pivaloylacetonitrile, 1,3-cyclopentanedione, and 4-hydroxycoumarin. The key step of the reaction was believed to involve the formation of a β-enamino ester and a sequential Michael addition to the in situ formed arylidene dicarbonyl compound.

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

Similar content being viewed by others

References

  1. Huisgen R (1969) Topics in heterocyclic chemistry. In: Castle R (ed), Chap 8. John Wiley and Sons, New York, p 223

  2. Huisgen R, Morikawa M, Herbig K, Brunn E (1967) 1,4-Dipolare cycloaddionen, dreikomponenten-reaktioben des Isochinolins mit acetylenedicarbonseaureester und verschiednen dopolarophilen. Chem Ber 100: 1094–1106. doi:10.1002/cber.19671000406

    Article  CAS  Google Scholar 

  3. Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L, Mathen JS, Balagopal L (2003) Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes. Acc Chem Res 36: 899–907. doi:10.1021/ar020258p

    Article  PubMed  CAS  Google Scholar 

  4. Nair V, Menon RS, Sreekanth A, Abhilash N, Biju AT (2006) Engaging zwitterions in carboncarbon and carbon nitrogen bond-forming reactions: a promising synthetic strategy. Acc Chem Res 39: 520–530. doi:10.1021/ar0502026

    Article  PubMed  CAS  Google Scholar 

  5. Kielland N, Lavilla R (2010) Recent developments in reissert-type multicomponent reaction. Top Heterocycl Chem 25: 127–168. doi:10.1007/7081_2010_42

    Article  CAS  Google Scholar 

  6. Shaabani A, Rezayan AH, Sarvary A (2011) Recent progress of isocyanide-based multicomponent reactions in Iran. Mol Divers 15: 41–68. doi:10.1007/s11030-010-9258-1

    Article  PubMed  CAS  Google Scholar 

  7. Nair V, Devipriya S, Suresh E (2008) Construction of heterocycles via 1,4-dipolar cycloaddition of quinoline–DMAD zwitterion with various dipolarophiles. Tetrahedron 64: 3567–3577. doi:10.1016/j.tet.2008.01.106

    Article  CAS  Google Scholar 

  8. Nair V, Devipriya S, Suresh E (2007) Efficient synthesis of [1,3]oxazino[2,3-a]quinoline derivatives by a novel 1,4-dipolar cycloaddition involving a quinoline–DMAD zwitterion and carbonyl compounds. Tetrahedron Lett 48: 3667–3670. doi:10.1016/j.tetlet.2007.03.123

    Article  CAS  Google Scholar 

  9. Yavari I, Mirzaei A, Moradi L, Khalili G (2010) Diastereoselective synthesis of spiro-functionalized tetraalkyl benzoisoquinopyrrolonaphthyridine-tetracarboxylates from isoquinoline, dialkyl acetylenedicarboxylates, and indane-1,3-dione. Tetrahedron Lett 51: 396–398. doi:10.1016/j.tetlet.2009.11.040

    Article  CAS  Google Scholar 

  10. Yavari I, Piltan M, Moradi L (2009) Synthesis of pyrrolo[2,1-a]-isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline. Tetrahedron 65: 2067–2071. doi:10.1016/j.tet.2009.01.001

    Article  CAS  Google Scholar 

  11. Harju K, Vesterinen J, Yli-Kauhaluoma J (2009) Solid-phase synthesis of amino acid Derived N-unsubstituted pyrazoles via sydnones. Org Lett 11: 2219–2221. doi:10.1021/ol900704b

    Article  PubMed  CAS  Google Scholar 

  12. Shibata Y, Noguchi K, Hirano M, Tanaka K (2008) Rhodium-catalyzed highly enantio- and diastereoselective cotrimerization of alkenes and dialkyl acetylenedicarboxylates leading to furylcyclopropanes. Org Lett 10: 2825–2828. doi:10.1021/ol800966f

    Article  PubMed  CAS  Google Scholar 

  13. Ma C, Ding HF, Wang YG (2006) Novel annulation reactions of aryl methyl ketenes with Zwitterions derived from dimethyl acetylenedicarboxylate and N-alkylimidazoles. Org Lett 8: 3133–3136. doi:10.1021/ol061126p

    Article  PubMed  CAS  Google Scholar 

  14. Yadav JS, Reddy BVS, Yadav NN, Gupta MK, Sridhar B (2008) Gold(III) chloride-catalyzed three-component reaction: A facile synthesis of alkynyl derivatives of 1,2-dihydroquinolines and isoquinolines. J Org Chem 73: 6857–6859. doi:10.1021/jo8007034

    Article  PubMed  CAS  Google Scholar 

  15. Ding HF, Zhang YP, Bian M, Yao WJ, Ma C (2008) Concise assembly of highly substituted furan-Fused 1,4-thiazepines and their Diels-Alder reactions with benzynes. J Org Chem 73: 578–584. doi:10.1021/jo702299m

    Article  PubMed  CAS  Google Scholar 

  16. Glotova T, Dvorko M, UshakovI. Chipanina N, Kazheva O, Chekhlov A, Dyachenko O, Gusarova N, Trofimov B (2009) Chemo-, regio- and stereospecific addition of amino acids to acylacetylenes: a facile synthesis of new N-acylvinyl derivatives of amino acids. Tetrahedron 65: 9814–9818. doi:10.1016/j.tet.2009.09.069

    Article  CAS  Google Scholar 

  17. Ziyaei-Halimehjani A, Saidi MR (2008) Synthesis of aza-Henry products and enamines in water by Michael addition of amines or thiols to activated unsaturated compounds. Tetrahedron Lett 49: 1244–1248. doi:10.1016/j.tetlet.2007.12.042

    Article  CAS  Google Scholar 

  18. Li X, Wang JY, Yu W, Wu LM (2009) PtCl2-catalyzed reactions of o-alkynylanilines with ethyl propiolate and dimethyl acetylenedicarboxylate. Tetrahedron 65: 1140–1146. doi:10.1016/j.tet.2008.11.095

    Article  CAS  Google Scholar 

  19. Zhu QH, Jiang HF, Li JH, Zhang M, Wang XJ, Qi CR (2010) l-Proline-catalyzed five-component domino reaction leading to multifunctionalized 1,2,3,4-tetrahydropyridines. Tetrahedron 66: 9721–9728. doi:10.1016/j.tet.2010.10.041

    Article  Google Scholar 

  20. Lue P, Greenhill JV (1996) Enaminones in heterocyclic synthesis. Adv Heterocycl Chem 67: 207–343

    Article  CAS  Google Scholar 

  21. Elassara AZ, El-Khair AA (2003) Recent developments in the chemistry of enaminones. Tetrahedron 59: 8463–8480. doi:10.1016/S0040-4020(03)01201-8

    Article  Google Scholar 

  22. Nguyen TB, Martel A, Dhal R, Dujardin G (2008) N-Benzyl aspartate nitrones: unprecedented single-step synthesis and [3 + 2] cycloaddition reactions with alkenes. Org Lett 10: 4493–4496. doi:10.1021/ol8017243

    Article  PubMed  CAS  Google Scholar 

  23. Fan MQ, Yan ZY, Liu WM, Liang YM (2005) Versatile access to C-4-substituted 2-amino-1,3-azoles from hydropyridines in oxidative conditions. J Org Chem 70: 8204–8207. doi:10.1021/jo050903g

    Article  PubMed  CAS  Google Scholar 

  24. Srikrishna A, Sridharan M, Prasad KR (2010) Stereochemical studies of 5-methyl-3-(substituted phenyl)-5-[(substituted phenyl) hydroxy methyl]-2-thiooxazolidin-4-ones. Tetrahedron Lett 51: 3654–3657. doi:10.1016/j.tetlet.2010.05.027

    Article  Google Scholar 

  25. Bezenšek J, Koleša T, Grošelj U, Wagger J, Stare K, Meden A, Svete J, Stanovnik B (2010) [2+2] Cycloaddition of electron-poor acetylenes to (E)-3-dimethylamino-1-heteroaryl-prop-2-en-1-ones: synthesis of highly functionalized 1-heteroaroyl-1,3-butadienes. Tetrahedron Lett 51: 3392–3397. doi:10.1016/j.tetlet.2010.04.106

    Article  Google Scholar 

  26. Singh P, Sharma P, Bisetty K, Mahajan M (2009) Cycloaddition reactions of cross-conjugated enaminones. Tetrahedron 65: 8478–8485. doi:10.1016/j.tet.2009.08.038

    Article  CAS  Google Scholar 

  27. Zewge D, Chen CY, Deer C, Dormer PG, Hughes DL (2007) A mild and efficient synthesis of 4-quinolones and quinolone heterocycles. J Org Chem 72: 4276–4279. doi:10.1021/jo070181o

    Article  PubMed  CAS  Google Scholar 

  28. Sun J, Xia EY, Wu Q, Yan CG (2010) Synthesis of polysubstituted dihydropyridines by four-component reactions of aromatic aldehydes, malononitrile, arylamines, and acetylenedicarboxylate. Org Lett 12: 3678–3681. doi:10.1021/ol101475b

    Article  PubMed  CAS  Google Scholar 

  29. Sun J, Xia EY, Wu Q, Yan CG (2011) Synthesis of 3,4-dihydropyridin-2(1H)-ones and 3,4-dihydro- 2H-pyrans via four-component reactions of aromatic aldehydes, cyclic 1,3-carbonyls, arylamines, and dimethyl acetylenedicarboxylate. ACS Comb Sci 13: 421–426. doi:10.1021/co200045t

    Article  PubMed  CAS  Google Scholar 

  30. Matsumoto S, Mori T, Akazome M (2010) Formation of 1,2-dihydroquinoline-3-carboxylic Acid derivatives from methyl 3-(arylamino)acrylates with hydrogen iodide. Synthesis 3615–3622. doi:10.1055/s-0030-1258229

  31. Kandeel AK, Vernon JMM (1987) Reactions of tertiary allylamines with dimethyl acetylenedicarboxylate. J Chem Soc Perkin Trans 1: 2023–2026. doi:10.1039/P19870002023

    Article  Google Scholar 

  32. Cho CS (2005) An efficient dealkylative addition of trialkylamines to dialkyl acetylenedicarboxylates in the presence of a metallic chloride. Tetrahedron Lett 46: 1415–1417. doi:10.1016/j.tetlet.2005.01.034

    Article  CAS  Google Scholar 

  33. Ziyaei-Halimehjani A, Saidi MR (2008) An efficient dealkylative addition of trialkylamines to dialkyl acetylenedicarboxylates in the presence of a metallic chloride. Tetrahedron Lett 49: 1244–1248. doi:10.1016/j.tetlet.2007.12.042

    Article  CAS  Google Scholar 

  34. Zhu QH, Jiang HF, Li JH, Zhang M, Wang XJ, Qi CR (2009) Practical synthesis and mechanistic study of polysubstituted tetrahydropyrimidines with use of domino multicomponent reactions. Tetrahedron 65: 4604–4613. doi:10.1016/j.tet.2009.03.071

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Chemistry & Chemical Engineering Yangzhou University, Yangzhou, 225002, China

    Yan Sun, Jing Sun & Chao-Guo Yan

Authors
  1. Yan Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jing Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chao-Guo Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chao-Guo Yan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sun, Y., Sun, J. & Yan, CG. Synthesis of polyfunctionalized acrylates via one-pot reactions of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds. Mol Divers 16, 163–171 (2012). https://doi.org/10.1007/s11030-011-9344-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-011-9344-z

Keywords

Search

Navigation