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Unsaturated carboxylic acids in the one-pot synthesis of novel derivatives of 3,4-dihydro-2H-thiopyran

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of α,β-unsaturated ketones and Lawesson’s reagent with maleic, itaconic, or 5-norbornene-2,3-dicarboxylic acid led to the corresponding 3,4-dihydro-2H-thiopyran anhydrides. As a result of the reaction of methacrylic acid, Lawesson’s reagent, and chalcone, 4-methyl-1,8-diphenyl-2,6-dithiabicyclo[2.2.2]octan-3-one is formed. The selectivity of the acylation of amines using the synthesized anhydrides was studied.

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References

  1. (a) Antipin, I. S.; Kazymova, M. A.; Kuznetsov, M. A.; Vasilyev, A. V.; Ishchenko, M. A.; Kiryushkin, A. A.; Kuznetsova, L. M.; Makarenko, S. V.; Ostrovskii, V. A.; Petrov, M. L.; Solod, O. V.; Trishin, Yu. G.; Yakovlev, I. P.; Nenajdenko, V. G.; Beloglazkina, E. K.; Beletskaya, I. P.; Ustynyuk, Yu. A.; Solov’ev, P. A.; Ivanov, I. V.; Malina, E. V.; Sivova, N. V.; Negrebetskii, V. V.; Baukov, Yu. I.; Pozharskaya, N. A.; Traven’, V. F.; Shchekotikhin, A. E.; Varlamov, A. V.; Borisova, T. N.; Lesina, Yu. A.; Krasnokutskaya, E. A.; Rogozhnikov, S. I.; Shurov, S. N.; Kustova, T. P.; Klyuev, M. V.; Khelevina, O. G.; Stuzhin, P. A.; Fedorov, A. Yu.; Gushchin, A. V.; Dodonov, V. A.; Kolobov, A. V.; Plakhtinskii, V. V.; Orlov, V. Yu.; Kriven’ko, A. P.; Fedotova, O. V.; Pchelintseva, N. V.; Charushin, V. N.; Chupakhin, O. N.; Klimochkin, Yu. N.; Klimochkina, A. Yu.; Kuryatnikov, V. N.; Malinovskaya, Yu. A.; Levina, A. S.; Zhuravlev, O. E.; Voronchikhina, L. I.; Fisyuk, A. S.; Aksenov, A. V.; Aksenov, N. A.; Aksenova, I. V. Russ. J. Org. Chem. 2017, 53, 1275. [Zh. Org. Khim. 2017, 53, 1257.] (b) Konovalov, A. I.; Antipin, I. S.; Burilov, V. A.; Madzhidov, T. I.; Kurbangalieva, A. R.; Nemtarev, A. V.; Solovieva, S. E.; Stoikov, I. I.; Mamedov, V. A.; Zakharova, L. Ya.; Gavrilova, E. L.; Sinyashin, O. G.; Balova, I. A.; Vasilyev, A. V.; Zenkevich, I. G.; Krasavin, M. Yu.; Kuznetsov, M. A.; Molchanov, A. P.; Novikov, M. S.; Nikolaev, V. A.; Rodina, L. L.; Khlebnikov, A. F.; Beletskaya, I. P.; Vatsadze, S. Z.; Gromov, S. P.; Zyk, N. V.; Lebedev, A. T.; Lemenovskii, D. A.; Petrosyan, V. S.; Nenaidenko, V. G.; Negrebetskii, V. V.; Baukov, Yu. I.; Shmigol’, T. A.; Korlyukov, A. A.; Tikhomirov, A. S.; Shchekotikhin, A. E.; Traven’, V. F.; Voskresenskii, L. G.; Zubkov, F. I.; Golubchikov, O. A.; Semeikin, A. S.; Berezin, D. B.; Stuzhin, P. A.; Filimonov, V. D.; Krasnokutskaya, E. A.; Fedorov, A. Yu.; Nyuchev, A. V.; Orlov, V. Yu.; Begunov, R. S.; Rusakov, A. I.; Kolobov, A. V.; Kofanov, E. R.; Fedotova, O. V.; Egorova, A. Yu.; Charushin, V. N.; Chupakhin, O. N.; Klimochkin, Yu. N.; Osyanin, V. A.; Reznikov, A. N.; Fisyuk, A. S.; Sagitullina, G. P.; Aksenov, A. V.; Aksenov, N. A.; Grachev, M. K.; Maslennikova, V. I.; Koroteev, M. P.; Brel’, A. K.; Lisina, S. V.; Medvedeva, S. M.; Shikhaliev, Kh. S.; Suboch, G. A.; Tovbis, M. S.; Mironovich, L. M.; Ivanov, S. M.; Kurbatov, S. V.; Kletskii, M. E.; Burov, O. N.; Kobrakov, K. I.; Kuznetsov, D. N. Russ. J. Org. Chem. 2018, 54, 157. [Zh. Org. Khim. 2018, 54, 161.]

  2. (a) Merkulova, Е. А.; Kolobov, А. V.; Ovchinnikov, K. L. RF patent № 2670977; Byull. Izobret. 2018, (30). (b) Merkulova, E. A.; Kolobov, A. V.; Ovchinnikov, K. L. Russ. Chem. Bull., Int. Ed. 2019, 68, 606. [Izv. Akad. Nauk, Ser. Khim. 2019, 606.]

  3. Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210.

    Article  CAS  Google Scholar 

  4. (a) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (b) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147.

  5. Bogdanowicz-Szwed, K.; Budzowski, A. Z. Naturforschung, B: J. Chem. Sci. 2002, 57, 637.

    CAS  Google Scholar 

  6. Rao, Y.; Li, X.; Nagorny, P.; Hayashida, J.; Danishefsky, S. J. Tetrahedron Lett. 2009, 50, 6684.

    Article  CAS  Google Scholar 

  7. (a) Scheibye, S.; Shabana, R.; Lawesson, S.-O.; Rømming, C. Tetrahedron 1982, 38, 993. (b) Przychodzeń, W. Eur. J. Org. Chem. 2005, 10, 2002.

  8. Kolobov, А. V. Doctoral (Chem.) Dissertation; Yaroslavl, 2007. https://www.dissercat.com/content/vitsinalnye-dikarbonovyekisloty-sintez-struktura-svoistva

  9. Gordon, А.; Ford, R. Sputnik khimika (The Chemist’s Companion [Russian translation]); Moscow: Mir, 1976, p. 301.

  10. Cinar, S. A.; Ercan, S.; Gunal, S. E.; Dogan I.; Aviyente, V. Org. Biomol. Chem. 2014, 12, 8079.

    Article  Google Scholar 

  11. Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061.

    Article  CAS  Google Scholar 

  12. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

  13. (a) Palatinus, L.; Chapuis, G. J. Appl. Crystallogr. 2007, 40, 786. (b) Palatinus, L.; Van der Lee, A. J. Appl. Crystallogr. 2008, 41, 975. (c) Palatinus, L.; Prathapa, S. J.; van Smaalen, S. J. Appl. Crystallogr. 2012, 45, 575.

  14. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

    Google Scholar 

  15. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Yaroslavl State Technical University, 88 Moskovsky Ave., Yaroslavl, 150023, Russia

    Ekaterina А. Merkulova, Aleksei V. Kolobov & Konstantin L. Ovchinnikov

  2. RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Victor N. Khrustalev

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Victor N. Khrustalev

  4. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Valentine G. Nenajdenko

Authors
  1. Ekaterina А. Merkulova
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  2. Aleksei V. Kolobov
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  3. Konstantin L. Ovchinnikov
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  4. Victor N. Khrustalev
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  5. Valentine G. Nenajdenko
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Correspondence to Ekaterina А. Merkulova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(3), 245–252

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Merkulova, E.А., Kolobov, A.V., Ovchinnikov, K.L. et al. Unsaturated carboxylic acids in the one-pot synthesis of novel derivatives of 3,4-dihydro-2H-thiopyran. Chem Heterocycl Comp 57, 245–252 (2021). https://doi.org/10.1007/s10593-021-02900-y

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  • DOI: https://doi.org/10.1007/s10593-021-02900-y

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