Skip to main content

Advertisement

SpringerLink
Log in

One-pot synthesis of methyl 4-amino-2,3,3-trisubstituted-1,1-dioxo-2,3-dihydro-1H-1λ6-isothiazole-5-carboxylates

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A range of aminonitriles, readily available by Strecker reaction, were forced to react with methyl 2-(chlorosulfonyl)acetate. Methyl 2-[[(cyanoalkyl)amino]sulfonyl]acetates formed on the first stage without isolation were converted to methyl 4-amino-2,3,3-trisubstituted-1,1-dioxo-2,3-dihydro-1H-1λ6-isothiazole-5-carboxylates via CSIC reaction using Et3N-mediated conditions in poor to high yields. The structure of the target compound was confirmed by X-ray diffraction study.

Graphical abstract

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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Winum J-Y, Scozzafava A, Montero J-L, Supuran CT (2005) Med Res Rev 25:186

    Article  CAS  PubMed  Google Scholar 

  2. Saeidian H, Abdoli M, Mirjafary Z (2015) Synthesis 47:1057

    Article  CAS  Google Scholar 

  3. Ghiasi M, Oskouie AA, Saeidian H (2012) Carbohydr Res 348:47

    Article  CAS  PubMed  Google Scholar 

  4. Spillane W, Malaubier J-B (2014) Chem Rev 114:2507

    Article  CAS  PubMed  Google Scholar 

  5. Fornarini S (1991) Mass spectrometry of sulfonic acids and their derivatives. In: Patai S, Rappoport Z (eds) The chemistry of sulphonic acids, esters and their derivatives. Wiley, Chichester, p 73

    Chapter  Google Scholar 

  6. Popova MV, Dobrydnev AV (2017) Chem Heterocycl Compd 53:492

    Article  CAS  Google Scholar 

  7. Cherney RJ, Mo R, Meyer DT, Hardman KD, Liu RQ, Covington MB, Qian M, Asserman ZR, Christ DD, Trzaskos JM, Newton RC, Decicco CP (2004) J Med Chem 47:2981

    Article  CAS  PubMed  Google Scholar 

  8. Binder D (1987) Thieno-1,2-thiazole derivatives, process for their preparation, and pharmaceutical compositions containing them. EP Patent 0,213,295, 11 Mar 1987

  9. Binder D (1987) Chem Abstr 107:96709

    Google Scholar 

  10. Abou-Gharbia MA, Schiehser GA, Childress SJ (1988) Piperazinoisothiazolones with psychotropic activity. US Patent 4,732,984, 22 Mar 1988

  11. Abou-Gharbia MA, Schiehser GA, Childress SJ (1988) Chem Abstr 108:112497

    Google Scholar 

  12. Gymer GE, Narayanaswami S, Richardson K (1990) Triazole antifungal agents. EP Patent 0,352,946, 31 Jan 1990

  13. Gymer GE, Narayanaswami S, Richardson K (1990) Chem Abstr 113:40728

    Google Scholar 

  14. Anderson DJ, Hester JB Jr (2001) Antibiotic sultam and sultone derived oxazolidinones. WO Patent 2001,032,657, 10 May 2001

  15. Anderson DJ, Hester JB Jr (2001) Chem Abstr 134:340497

    Google Scholar 

  16. Stachel H-D, Odlerova Z, Waisser K (1997) Collect Czech Chem Commun 62:510

    Article  CAS  Google Scholar 

  17. Ingate ST, Marco JL, Witvrouw M, Pannecouque C, De Clercq E (1997) Tetrahedron 53:17795

    Article  CAS  Google Scholar 

  18. Van Nhien AN, Tomassi C, Len C, Marco-Contelles JL, Balzarini J, Pannecouque C, De Clercq E, Postel D (2005) J Med Chem 48:4276

    Article  CAS  Google Scholar 

  19. Dobrydnev AV, Popova MV, Saffon-Merceron N, Listunov D, Volovenko YM (2015) Synthesis 47:2523

    Article  CAS  Google Scholar 

  20. Popova MV, Dobrydnev AV, Dyachenko MS, Duhayon C, Listunov D, Volovenko YM (2017) Monats Chem 148:939

    Article  CAS  Google Scholar 

  21. Brodney MA, Efremov IV, Helal CJ, O’Neill BT (2013) Novel sultam compounds. US Patent, US20130150376, 13 Jun 2013

  22. Brodney MA, Efremov IV, Helal CJ, O’Neill BT (2011) Chem Abstr 155:536135

    Google Scholar 

  23. Marco JL, Ingate ST, Jaime C, Beá I (2000) Tetrahedron 56:2523

    Article  CAS  Google Scholar 

  24. Stachel H-D, Zimmer B, Eckl E, Semmlinger K, Weigand W, Wuensch R, Mayer P (2005) Helv Chim Acta 88:1208

    Article  CAS  Google Scholar 

  25. Schachtner JE, Zoukas T, Stachel H-D, Polborn K, Noeth H (1999) J Heterocycl Chem 36:161

    Article  CAS  Google Scholar 

  26. Clerici F, Ferraris F, Gelmi ML (1995) Tetrahedron 51:12351

    Article  CAS  Google Scholar 

  27. Clerici F, Gelmi ML, Monzani C, Pocar D, Sala A (2006) J Heterocycl Chem 43:1045

    Article  CAS  Google Scholar 

  28. Blackburn J, Molyneux G, Pitard A, Rice CR, Page MI, Afshinjavid S, Javid FA, Coles SJ, Hortond PN, Hemming K (2016) Org Biomol Chem 14:2134

    Article  CAS  PubMed  Google Scholar 

  29. Marco JL, Ingate ST, Chinchón PM (1999) Tetrahedron 55:7625

    Article  CAS  Google Scholar 

  30. Dobrydnev AV, Vashchenko BV, Volovenko YM (2018) Tetrahedron Lett 59:1581

    Article  CAS  Google Scholar 

  31. Oliver JE, Demilo AB (1975) Synthesis 5:321

    Article  Google Scholar 

  32. Stork G, Szajewski PR (1974) J Am Chem Soc 96:5787

    Article  CAS  PubMed  Google Scholar 

  33. Mai K, Patil G (1985) Synth Commun 15:157

    Article  CAS  Google Scholar 

  34. Ralph A, Jacobson RA (1945) J Am Chem Soc 67:1996

    Article  Google Scholar 

  35. Hawkins WL, Biggs BS (1949) J Am Chem Soc 71:2530

    Article  CAS  Google Scholar 

  36. Alvarez RM, Vazquez AS, Hananck M, Subramanian LR (1996) J Phys Org Chem 9:227

    Article  Google Scholar 

  37. Baeza A, Nájera C, Sansano JM (2007) Synthesis 8:1230

    Google Scholar 

  38. Kalir A, Teomy S, Amir A, Fuchs P, Lee SA, Holsztynska EJ, Rocki W, Domino EF (1984) J Med Chem 27:1267

    Article  CAS  PubMed  Google Scholar 

  39. Rafiee E, Rashidzadeh S, Joshaghani M, Chalabeh H, Afza K (2008) Synth Commun 38:2741

    Article  CAS  Google Scholar 

  40. Prakash GKS, Panja C, Do C, Mathew T, Olah GA (2007) Synlett 15:2395

    Article  CAS  Google Scholar 

  41. Bakthavatchalam R, Ihle DC, Capitosti SM, Wustrow DJ, Yuan J (2009) Heteroaryl amide analogues. International Patent, WO2009108551, 3 Sep 2009

  42. Bakthavatchalam R, Ihle DC, Capitosti SM, Wustrow DJ, Yuan J (2009) Chem Abstr 151:337205

    Google Scholar 

  43. Mobaraki A, Movassagh B, Karimi B (2014) ACS Comb Sci 16:352

    Article  CAS  PubMed  Google Scholar 

  44. Matsumoto K, Kim JC, Hayashia N, Jennerb G (2002) Tetrahedron Lett 43:9167

    Article  CAS  Google Scholar 

  45. Hanafusa T, Ichihara J, Ashida T (1987) Chem Lett 16:687

    Article  Google Scholar 

  46. Perrin DD, Armarego IF, Perrin DR (1980) Purification of laboratory chemicals, 2nd edn. Pergamon Press, New York

    Google Scholar 

  47. Sheldrick GM (2015) Acta Cryst A 71:3

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Bohdan Vashchenko would like to show our gratitude to Vladyslava Prykhodko for sharing her pearls of wisdom with us during the course of this research. The authors also thank Tatiana Vashchenko for a fellowship and technical support.

Author information

Authors and Affiliations

  1. Chemistry Department, Taras Shevchenko National University of Kiev, Lva Tolstoho Street 12, Kiev, 01033, Ukraine

    Alexey V. Dobrydnev, Bohdan V. Vashchenko, Kyrylo O. Bisikalo & Yulian M. Volovenko

  2. SMC Ecopharm Ltd., Naberezhno-Korchuvatska Street 136-B, Kiev, 03045, Ukraine

    Alexey V. Dobrydnev

  3. Division of Functional Materials Chemistry, SSI “Institute for Single Crystals” National Academy of Science of Ukraine, Nauky Avenue 60, Kharkiv, 61001, Ukraine

    Iryna S. Konovalova

Authors
  1. Alexey V. Dobrydnev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bohdan V. Vashchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Iryna S. Konovalova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kyrylo O. Bisikalo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yulian M. Volovenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alexey V. Dobrydnev.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 7254 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dobrydnev, A.V., Vashchenko, B.V., Konovalova, I.S. et al. One-pot synthesis of methyl 4-amino-2,3,3-trisubstituted-1,1-dioxo-2,3-dihydro-1H-1λ6-isothiazole-5-carboxylates. Monatsh Chem 149, 1827–1833 (2018). https://doi.org/10.1007/s00706-018-2241-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2241-8

Keywords

Search

Navigation