Skip to main content
SpringerLink
Log in

Synthesis and Aromatization of Ethyl Esters of cis-4-(Methanesulfonyl)-cis-5-arylprolines. Unusual Synthesis of 5-Aryl-2-acetylpyrrole

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

1-Bromovinyl and vinyl methyl sulfones undergo 1,3-dipolar cycloaddition reactions with azomethinylides generated in situ from ethyl N-benzylideneglycinates under the action of silver acetate and triethylamine (toluene, 20°C, 48 h) to form ethyl esters of 4-methanesulfonyl-substituted cis-5-arylprolines. The bromo-substituted adducts convert into the corresponding ethyl 5-aryl-1H-pyrrole-2-carboxylates under heating with an excess of DBU in THF or sodium ethylate in ethanol. Heating of the adducts of vinyl methyl sulfone with sodium ethylate in ethanol in sealed ampules at 90°C leads to mixtures of ethyl 5-aryl-1H-pyrrole-2-carboxylates and 5-aryl-2-acetylpyrroles.

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
Fig. 1.
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Loya, S., Rudi, A., Kashman, Y., and Hizi, A., Biochem. J., 1999, vol. 344, p. 85. https://doi.org/10.1042/bj3440085

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Pindur, U., Kim, Y.-S., and Mehrabani, F., Curr. Med. Chem., 1999, vol. 6, p. 29.

    CAS  PubMed  Google Scholar 

  3. Kashman, Y., Koren-Goldshlager, G., Gravalos, M.D.G., and Schleyer, M., Tetrahedron Lett., 1999, vol. 40, p. 997. https://doi.org/10.1016/S0040-4039(98)02467-8

    Article  CAS  Google Scholar 

  4. Biava, M., Fioravanti, R., Porretta, G.C., Deidda, D., Maullu, C., and Pompei, R., Bioorg. Med. Chem. Lett., 1999, vol. 9, p. 2983. https://doi.org/10.1016/S0960-894X(99)00510-7

    Article  CAS  PubMed  Google Scholar 

  5. Mortensen, D.S., Rodriguez, A.L., Carlson, K.E., Sun, J., Katzenellenbogen, B.S., and Katzenellenbogen, J.A., J. Med. Chem., 2001, vol. 44, p. 3838. https://doi.org/10.1021/jm010211u

    Article  CAS  PubMed  Google Scholar 

  6. Bellina, F. and Rossi, R., Tetrahedron, 2006, vol. 62, p. 7213. https://doi.org/10.1016/j.tet.2006.05.024

    Article  CAS  Google Scholar 

  7. Knorr, L., Ber. Dtsch. Chem. Ges., 1884, vol. 17, p. 1635. https://doi.org/10.1002/cber.18840170220

    Article  Google Scholar 

  8. Paal, C., Ber. Dtsch. Chem. Ges., 1885, vol. 18, p. 367. https://doi.org/10.1002/cber.18850180175

    Article  Google Scholar 

  9. Braun, R.U. and Mueller, T.J.J., Synthesis, 2004, p. 2391. https://doi.org/10.1055/s-2004-831192

  10. Hantzsch, A., Ber. Dtsch. Chem. Ges., 1890, vol. 23, p. 1474. https://doi.org/10.1002/cber.189002301243

    Article  Google Scholar 

  11. Padwa, A., Gruber, R., and Pashayan, D., J. Org. Chem., 1968, vol. 33, p. 454. https://doi.org/10.1021/jo01265a108

    Article  CAS  Google Scholar 

  12. Balme, G., Angew. Chem., Int. Ed., 2004, vol. 43, p. 6238. https://doi.org/10.1002/anie.200461073

    Article  CAS  Google Scholar 

  13. Tejedor, D., Gonzalez-Cruz, D., Garcia-Tellado, F., Marrero-Tellado, J.J., and Rodriguez, M.L., J. Am. Chem. Soc., 2004, vol. 126, p. 8390. https://doi.org/10.1021/ja047396p

    Article  CAS  PubMed  Google Scholar 

  14. Joshi, U., Pipelier, M., Naud, S., and Dubreuil, D., Curr. Org. Chem., 2005, vol. 9, p. 261. https://doi.org/10.2174/1385272053369132

    Article  CAS  Google Scholar 

  15. Cyr, D.J.S., Martin, N., and Arndtsen, B.A., Org. Lett., 2007, vol. 9, p. 449. https://doi.org/10.1021/ol062773j

    Article  CAS  PubMed  Google Scholar 

  16. Knight, D.W., Redferna, A.L., and Gilmore, J., Synlett, 1998, p. 731. https://doi.org/10.1055/s-1998-1768

  17. Knight, D.W., Redferna, A.L., and Gilmore, J., J. Chem. Soc., Perkin Trans. 1, 2001, p. 2874. https://doi.org/10.1039/B106739G

  18. Gupton, J.T., Krolikowski, D.A., Yu, R.H., and Vu, P., J. Org. Chem., 1992, vol. 57, p. 5480. https://doi.org/10.1021/jo00046a033

    Article  CAS  Google Scholar 

  19. Barton, D.H.R., Kervagoret, J., and Zard, S.Z., Tetrahedron, 1990, vol. 46, p. 7587. https://doi.org/10.1016/S0040-4020(01)89069-4

    Article  CAS  Google Scholar 

  20. Arrieta, A., Otaegui, D., Zubia, A., Cossío, F.P., Díaz-Ortiz, A., de la Hoz, A., Herrero, M.A., Prieto, P., Foces-Foces, C., Pizarro, J.L., and Arriortua, M.I., J. Org. Chem., 2007, vol. 72, p. 4313. https://doi.org/10.1021/jo062672z

    Article  CAS  PubMed  Google Scholar 

  21. Bergner, I. and Opatz, T., J. Org. Chem., 2007, vol. 72, p. 7083. https://doi.org/10.1021/jo070426x

    Article  CAS  PubMed  Google Scholar 

  22. Bergner, I., Wiebe, C., Meyer, N., and Opatz, T., J. Org. Chem., 2009, vol. 74, p. 8243. https://doi.org/10.1021/jo901759u

    Article  CAS  PubMed  Google Scholar 

  23. Ruano, J.L.G., Tito, A., and Peromingo, M.T., J. Org. Chem., 2002, vol. 67, p. 981. https://doi.org/10.1021/jo010797s

    Article  CAS  Google Scholar 

  24. Ruano, J.L.G., Tito, A., and Peromingo, M.T., J. Org. Chem., 2003, vol. 68, p. 10013. https://doi.org/10.1021/jo035369w

    Article  CAS  Google Scholar 

  25. Heine, H.W. and Peavy, R., Tetrahedron Lett., 1965, p. 3123. https://doi.org/10.1016/S0040-4039(01)89232-7

  26. Haake, G., Struve, D., and Montforts, F.-P., Tetrahedron Lett., 1994, vol. 35, p. 9703. https://doi.org/10.1016/0040-4039(94)88364-5

    Article  CAS  Google Scholar 

  27. Lygin, A.V., Larionov, O.V., Korotkov, V.S., and de Meijere, A., Chem. Eur. J., 2009, vol. 15, p. 227. https://doi.org/10.1002/chem.200801395

    Article  CAS  PubMed  Google Scholar 

  28. Lygin, A.V. and de Meijere, A., Angew. Chem., Int. Ed., 2010, vol. 49, p. 9094. https://doi.org/10.1002/anie.201000723

    Article  CAS  Google Scholar 

  29. Abel, Y., Haake, E., Haake, G., Schmidt, W., Struve, D., Walter, A., and Montforts, F.-P., Helv. Chim. Acta, 1998, vol. 81, p. 1978. https://doi.org/10.1002/(SICI)1522-2675(19981111)81:

    Article  CAS  Google Scholar 

  30. López-Pérez, A., Adrio, J., and Carretero, J.C., J. Am. Chem. Soc., 2008, vol. 130, p. 10084. https://doi.org/10.1021/ja804021m

    Article  CAS  PubMed  Google Scholar 

  31. López-Pérez, A., Adrio, J., and Carretero, J.C., Angew. Chem., Int. Ed., 2009, vol. 48, p. 340. https://doi.org/10.1002/anie.200805063

    Article  CAS  Google Scholar 

  32. Robles-Machín, R., González-Esguevillas, M., Adrio, J., and Carretero, J.C., J. Org. Chem., 2010, vol. 75, p. 233. https://doi.org/10.1021/jo902103z

    Article  CAS  PubMed  Google Scholar 

  33. Robles-Machín, R., López-Pérez, A., González-Esguevillas, M., Adrio, J., and Carretero, J.C., Chem. Eur. J., 2010, vol. 16, p. 9864. https://doi.org/10.1002/chem.201000742

    Article  CAS  PubMed  Google Scholar 

  34. Kudryavtsev, K.V., Ivantcova, P.M., Churakov, A.V., and Vasin, V.A., Tetrahedron Lett., 2012, vol. 53, p. 4300. https://doi.org/10.1016/j.tetlet.2012.05.160

    Article  CAS  Google Scholar 

  35. Blaney, P., Grigg, R., Rankovic, Z., Thornton-Pett, M., and Xu, J., Tetrahedron, 2002, vol. 58, p. 1719. https://doi.org/10.1016/S0040-4020(02)00029-7

    Article  CAS  Google Scholar 

  36. Vasin, V.A., Kalyazin, V.A., Petrov, P.S., and Somov, N.V., Russ. J. Org. Chem., 2019, vol. 55, p. 426. https://doi.org/10.1134/S107042801904002X

    Article  CAS  Google Scholar 

  37. Casas, J., Grigg, R., Najera, C., and Sansano, J.M., Eur. J. Org. Chem., 2001, vol. 123, p. 1971. https://doi.org/10.1002/1099-0690(200105)2001:

    Article  Google Scholar 

  38. Eelder, T., Gregory, L.C., Orozco, A., Pflug, J.L., Wiens, P.S., and Wilkinson, T.J., Synth. Commun., 1989, vol. 19, p. 763. https://doi.org/10.1080/00397918908050991

    Article  Google Scholar 

  39. Evanguelidou, E.K. and McEwen, W.E., J. Org. Chem., 1966, vol. 31, p. 4110. https://doi.org/10.1021/jo01350a056

    Article  CAS  Google Scholar 

  40. Gupton, J.T., Petrich, S.A., Smith, L.L., Bruce, M.A., Du, K.X., Dueno, E.E., Jones, C.R., and Sikorski, J.A., Tetrahedron, 1996, vol. 52, p. 6879. https://doi.org/10.1016/0040-4020(96)00338-9

    Article  CAS  Google Scholar 

  41. Schkurko, O.P. and Mamaev, V.P., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1967, vol. 6, p. 98.

    Google Scholar 

  42. Gaist, B. and Knittel, D., Monatsh. Chem., 1988, vol. 119, p. 571. https://doi.org/10.1007/BF00809209

    Article  Google Scholar 

  43. Chou, Sh.-Sh.P. and Yuan, T.-M., Synthesis, 1991, vol. 1991, p. 171. https://doi.org/10.1055/s-1991-26409

    Article  Google Scholar 

  44. Gaillot, J.-M., Gelas-Mialhe, Y., and Vessiere, R., Can. J. Chem., 1979, vol. 57, p. 1958. https://doi.org/10.1139/v79-314

    Article  CAS  Google Scholar 

  45. Buckley, G.D., Charlish, J.L., and Rose, J.D., J. Chem. Soc., 1947, p. 1514. https://doi.org/10.1039/JR9470001514

  46. Oxford Diffraction Ltd, version 1.171.36.21, release 14-08-2012, CrysAlis171.NET.

  47. Clark, R.C. and Reid, J.S., Acta Crystallogr., Sect. A, 1995, vol. 51, p. 887. https://doi.org/10.1107/S0108767395007367

    Article  Google Scholar 

  48. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370

    Article  CAS  Google Scholar 

  49. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837. https://doi.org/10.1107/S0021889899006020

    Article  CAS  Google Scholar 

  50. Farrugia, L.J., J. Appl. Crystallogr., 2012, vol. 45, p. 849. https://doi.org/10.1107/S0021889812029111

    Article  CAS  Google Scholar 

Download references

Funding

The work was supported by the Ministry of Science and Higher Education of the Russian Federation through the State order no. 0729-2020-0058.

Author information

Authors and Affiliations

  1. Ogarev Mordovia State University, 430005, Saransk, Russia

    P. S. Petrov & V. A. Kalyazin

  2. Lobachevskii Nizhny Novgorod State University, 603950, Nizhny Novgorod, Russia

    N. V. Somov

Authors
  1. P. S. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Kalyazin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. V. Somov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to P. S. Petrov.

Ethics declarations

The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 2, pp. 201–211 https://doi.org/10.31857/S0514749221020063.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Petrov, P.S., Kalyazin, V.A. & Somov, N.V. Synthesis and Aromatization of Ethyl Esters of cis-4-(Methanesulfonyl)-cis-5-arylprolines. Unusual Synthesis of 5-Aryl-2-acetylpyrrole. Russ J Org Chem 57, 170–179 (2021). https://doi.org/10.1134/S1070428021020068

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021020068

Keywords:

Search

Navigation