Skip to main content
Log in

Different regiochemical outcomes in annulation reactions of pyridine-2-sulfenyl chloride with phenyl vinyl chalcogenides and allyl phenyl chalcogenides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Annulation reactions of pyridine-2-sulfenyl chloride with phenyl vinyl chalcogenides and allyl phenyl chalcogenides proceeded regioselectively, but with different regiochemical outcomes and led to the formation of new 2- and 3-substituted [1,3]thiazolo[3,2-a]-pyridinium derivatives in 90–100% yields.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. (a) El-Gaby, M. S. A.; Al-Sehemi, A. G.; Mohamed, Y. A.; Ammar, Y. A. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 631. (b) El-Hag Ali, G. A.; Khalil, A. K.; Lamphon, R. Q.; El-Maghraby, A. A. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1909. (c) El-Maghraby, A. A.; El-Hag Ali, G. A. M.; Ahmed, A. H. A.; El-Gaby, M. S. A. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 293.

  2. (a) Shi, F.; Li, C.; Xia, M.; Miao, K.; Zhao, Y.; Tu, S.; Zheng, W.; Zhang, G.; Ma, N. Bioorg. Med. Chem. Lett. 2009, 19, 5565. (b) Walker, K. A.; Sjogren, E. B.; Matthews, T. R. J. Med. Chem. 1985, 28, 1673.

  3. Park, H.; Hwang, K. Y.; Oh, K. H.; Kim, Y. H.; Lee, J. Y.; Kim, K. Bioorg. Med. Chem. 2008, 16, 284.

    Article  CAS  Google Scholar 

  4. Haddach, M.; Schwaebe, M. K.; Michaux, J.; Nagasawa, J.; O'Brien, S. E.; Whitten, J. P.; Pierre, F.; Kerdoncuff, P.; Darjania, L.; Stansfield, R.; Drygin, D.; Anderes, K.; Proffitt, C.; Bliesath, J.; Siddiqui-Jain, A.; Omori, M.; Huser, N.; Rice, W. G.; Ryckman, D. M. ACS Med. Chem. Lett. 2012, 3, 602.

    Article  CAS  Google Scholar 

  5. (a) Borisov, A. V.; Osmanov, V. K.; Borisova, G. N.; Matsulevich, Zh. V.; Fukin, G. K. Mendeleev Commun. 2009, 19, 49. (b) Borisov, A. V.; Matsulevich, Zh. V.; Osmanov, V. K.; Borisova, G. N.; Mammadova, G. Z.; Maharramov, A. M.; Khrustalev, V. N. Chem. Heterocycl. Compd. 2012, 48, 1085. [Khim. Geterotsikl. Soedin. 2012, 1167.]

  6. (a) Potapov, V. A.; Ishigeev, R. S.; Shkurchenko, I. V.; Zinchenko, S. V.; Amosova, S. V. Molecules 2020, 25, 376. (b) Potapov, V. A.; Musalova, M. V.; Ishigeev, R. S.; Musalov, M. V.; Panov, V. A.; Khabibulina, A. G.; Amosova, S. V.; Bhasin, K. K. Tetrahedron Lett. 2016, 57, 5341.

  7. (a) Potapov, V. A.; Ishigeev, R. S.; Amosova, S. V.; Borodina, T. N. Tetrahedron Lett. 2019, 60, 475. (b) Potapov, V. A.; Ishigeev, R. S.; Amosova, S. V. Russ. J. Org. Chem. 2016, 52, 918. [Zh. Org. Khim. 2016, 52, 922.] (c) Potapov, V. A.; Malinovich, D. A.; Amosova, S. V.; Rusakov, Yu. Yu.; Bhasin, K. K. Chem. Heterocycl. Compd. 2012, 48, 1129. [Khim. Geterotsikl. Soedin. 2012, 1208.]

  8. (a) Ishigeev, R. S.; Potapov, V. A.; Amosova, S. V. Russ. J. Org. Chem. 2018, 54, 1262. [Zh. Org. Khim. 2018, 54, 1248.] (b) Potapov, V. A.; Ishigeev, R. S.; Amosova, S. V.; Zinchenko, S. V. Russ. Chem. Bull., Int. Ed. 2018, 67, 2326. [Izv. Akad. Nauk, Ser. Khim. 2018, 2326.] (c) Potapov, V. A.; Ishigeev, R. S.; Shkurchenko, I. V.; Amosova, S. V. Russ. J. Gen. Chem. 2019, 89, 2601. [Zh. Obshch. Khim. 2019, 89, 1965.]

  9. (a) Trofimov, B. A. Geteroatomnye proizvodnye atsetilena. Novye polifunktsional'nye monomery, reagenty i poluprodukty (Heteroatom-containing Derivatives of Acetylene. New Polyfunctional Monomers, Reagents, and Intermediates [in Russian]); Nauka: Moscow, 1981. (b) Nedolya, N. A.; Trofimov, B. A. Sulfur Rep. 1984, 15, 399

  10. Trofimov, B. A.; Amosova, S. V. Divinilsul'fid i ego proizvodnye (Divinyl Sulfide and its Derivatives [in Russian]); Nauka: Novosibirsk, 1983, c. 135.

  11. Klimova, V. A. Osnovnye mikrometody analiza organicheskikh soedinenii (The Main Methods for Microanalysis of Organic Compounds [in Russian]); Abramova, V. L., Ed.; Khimiya: Moscow, 1975, p. 104.

Download references

Spectral characterization was performed using the equipment at the Baikal Collective Use Analytical Center of the Siberian Branch of the Russian Academy of Sciences.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Vladimir A. Potapov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1226–1229

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Potapov, V.A., Ishigeev, R.S., Shkurchenko, I.V. et al. Different regiochemical outcomes in annulation reactions of pyridine-2-sulfenyl chloride with phenyl vinyl chalcogenides and allyl phenyl chalcogenides. Chem Heterocycl Comp 56, 1226–1229 (2020). https://doi.org/10.1007/s10593-020-02803-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02803-4

Keywords

Navigation