Skip to main content

Advertisement

SpringerLink
Log in

1,3-Dioxacyclanes: synthesis based on petrochemicals, chemical transformations, and applications

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The key results of research in the field of development of methods and approaches to the production of cyclic acetals based on petrochemical products are reviewed. The use of 1,3-dioxacyclanes in the synthesis of the series of practically important compounds, including biologically active ones, is briefly mentioned. The application of 1,3-dioxacycloalkanes in the synthesis of polyfunctional heterocyclic compounds are particularly considered.

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

References

  1. Product Class 8: 1,3-Dioxanes, 1,3-Dioxepanes, and Larger-Ring O/O Acetals. In Category 4, Compounds with Two Carbon Heteroatom Bonds, Ed. S. L. Warriner, Verlag KG, Stuttgart, 2007, Vol. 29; pp. 487–613; DOI: https://doi.org/10.1055/sos-SD-029-00478.2.

    Google Scholar 

  2. Protection for the Carbonyl Group, in Greene’s Protective Groups in Organic Synthesis, Fourth Edition, Eds P. G. M. Wuts, T. W. Greene, John Wiley and Sons, 2006, pp. 431–532; DOI: https://doi.org/10.1002/9780470053485.ch4.

  3. G. A. Tolstikov, T. G. Tolstikova, E.E. Shul’ts, S. E. Tolstikov, M. V. Khvostov, Smolyanye kisloty khvoinykh Rossii. Khimiya, farmakologiya [Resin Acids of Conifers in Russia. Chemistry, Pharmacology], Akad. Izd. GEO, Novosibirsk, 2011, pp. 395 (in Russian).

    Google Scholar 

  4. M. J. Climent, A. Velty, A. Corma, Green Chem., 2002, 4, 565; DOI: https://doi.org/10.1039/B207506G.

    Article  CAS  Google Scholar 

  5. J. Dorsky, The Chemistry of Synthetic Raw Materials Production. In Perfumes: Art, Science and Technology, Eds P. M. Müller, D. Lamparsky, Springer Netherlands, Dordrecht, 1994, pp. 399–420; DOI: https://doi.org/10.1007/978-94-011-3826-0_14.

    Chapter  Google Scholar 

  6. M. D. Ranken, R. C. Kill, C. Baker, Miscellaneous Food Ingredients, in Food Industries Manual, Eds M. D. Ranken, R. C. Kill, C. Baker, Springer, Boston, 1997, pp. 480–498; DOI: https://doi.org/10.1007/978-1-4613-1129-4_14.

    Chapter  Google Scholar 

  7. M. Honma, M. Yamada, M. Yasui, K. Horibata, K. Sugiyama, K. Masumura, Toxicol. Rep., 2022, 9, 1008; DOI: https://doi.org/10.1016/j.toxrep.2022.04.026.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. T. Rady, L. Turelli, M. Nothisen, E. Tobaldi, S. Erb, F. Thoreau, O. Hernandez-Alba, S. Cianferani, F. Daubeuf, A. Wagner, G. Chaubet, Bioconjugate Chem., 2022, 33, 1860; DOI: https://doi.org/10.1021/acs.bioconjchem.2c003

    Article  CAS  Google Scholar 

  9. A. S. Hamidi, M. A. Hadis, W. M. Palin, Dental Mater., 2022, 38, 1330; DOI: S010956412200152X.

    Article  CAS  Google Scholar 

  10. K. A. Berchtold, B. Hacioğlu, J. Nie, N. B. Cramer, J. W. Stansbury, C. Nowman, Macromolecules, 2009, 42, 2433; DOI: https://doi.org/10.1021/ma802406j.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. C. J. A. Mota, C. X. A. da Silva, N. Rosenbach, J. Costa, F. da Silva, Energy and Fuels, 2010, 24, 2733; DOI: https://doi.org/10.1021/ef9015735.

    Article  CAS  Google Scholar 

  12. D. Zhang, Y. Wei, K. Chen, H. Gong, S. Han, J. Guo, X. Li, J. Zhang, J. Biomed. Nanotechnol., 2015, 11, 923; DOI https://doi.org/10.1166/jbn.2015.2009.

    Article  CAS  PubMed  Google Scholar 

  13. A. V. Tugarova, A. A. Kamnev, A. N. Kazakova, S. S. Zlotskii, Russ. J. Gen. Chem., 2014, 84, 1930; DOI: https://doi.org/10.1134/S1070363214100119.

    Article  CAS  Google Scholar 

  14. G. A. Tolstikov, L. A. Baltina, V. P. Grankina, R. M. Kondratenko, T. G. Tolstikova, Solodka: bioraznoobrazie, khimiya, primenenie v meditsine [Licorice: Biodiversity, Chemistry, and Application in Medicine], Akad. Izd. GEO, Novosibirsk, 2007, 307 pp. (in Russian).

    Google Scholar 

  15. V. V. Loza, Z. R. Valiullina, M. S. Miftakhov, Russ. Chem. Bull., 2021, 70, 1; DOI: https://doi.org/10.1007/s11172-021-3052-3.

    Article  CAS  Google Scholar 

  16. S. M. Salikhov, L. K. Faizullina, F. A. Valeev, Russ. Chem. Bull., 2020, 69, 1933; DOI: https://doi.org/10.1007/s11172-020-2981-6.

    Article  CAS  Google Scholar 

  17. E. V. Buravlev, I. V. Fedorova, O. G. Shevchenko, A. V. Kutchin, Russ. Chem. Bull., 2019, 68, 1558; DOI: https://doi.org/10.1007/s11172-019-2592-2.

    Article  CAS  Google Scholar 

  18. S. S. Zlotskii, I. A. Sultanbekova, Izv. VUZov. Khim. Khim. Tekhnol. [Bulletin of Higher Educational Institutions. Chem. Chem. Technol.], 2008, 51, 3 (in Russian).

    CAS  Google Scholar 

  19. A. A. Bogomazova, N. N. Mikhailova, S. S. Zlotskii, Sovremennaya khimiya tsiklicheskikh atsetalei. Poluchenie. Reaktsii. Svoistva [Modern Chemistry of Cyclic Acetals. Preparation, Reactions, and Properties], LAP LAMBERT, Germany, 2012, p. 87 (in Russian).

    Google Scholar 

  20. S. D. Varfolomeev, V. B. Volieva, S. V. Usachev, I. S. Belostotskaya, N. L. Komissarova, A. V. Malkova, A. I. Nekhaev, A. L. Maksimov, G. G. Makarov, Catalysis in Industry (Engl. Transl.), 2011, 3, 11; DOI: https://doi.org/10.1134/S207005041101017X.

    Article  Google Scholar 

  21. A. L. Maximov, A. I. Nekhaev, D. N. Ramazanov, Petrol. Chem. (Eng l. Transl.), 2015, 55, 1; DOI: https://doi.org/10.1134/S0965544115010107.

    CAS  Google Scholar 

  22. L. Sekerová, M. Spáčilová, E. Vyskočilová, J. Krupka, L. Červený, Reaction Kinetics, Mechanisms and Catalysis, 2019, 127, 727; DOI: https://doi.org/10.1007/s11144-019-01595-9.

    Article  Google Scholar 

  23. D. N. Ramazanov, A. I. Nekhaev, V. O. Samoilov, A. L. Maximov, A. Dzhumbe, E. V. Egorova, Petrol. Chem. (Engl.Transl.), 2015, 55, 140; DOI: https://doi.org/10.7868/S002824211502015X.

    CAS  Google Scholar 

  24. S. Ammaji, G. S. Rao, K. V. R. Chary, Appl. Petrochem. Res., 2018, 8, 107; DOI: https://doi.org/10.1007/s13203-018-0197-6.

    Article  CAS  Google Scholar 

  25. L. P. Ozorio, R. Pianzolli, M. B. S. Mota, C. J. A. Mota, J. Braz. Chem. Soc., 2012, 23; DOI:https://doi.org/10.1590/S0103-50532012000500019.

  26. R. Sultanova, S. Borisevich, G. Raskil’dina, J. Borisova, I. Baykova, L. Spirikhin, S. Khursan, S. Zlotsky, J. Chin. Chem. Soc., 2020, 67, 1144; DOI: https://doi.org/10.1002/jccs.201900401.

    Article  CAS  Google Scholar 

  27. J. Deutsch, A. Martin, H. Lieske, J. Catal., 2007, 245, 428; DOI: https://doi.org/10.1016/j.jcat.2006.11.006.

    Article  CAS  Google Scholar 

  28. B. Mallesham, P. Sudarsanam, G. Raju, B. M. Reddy, Green Chem., 2013, 15, 478; DOI: https://doi.org/10.1039/C2GC36152C.

    Article  CAS  Google Scholar 

  29. A. V. Kutikov, A. A. Bogomazova, N. N. Mikhailova, Sovr. Nauchn. Issledovaniya i Razrabotki [Modern Research and Developments], 2018, 3, 330 (in Russian).

    Google Scholar 

  30. Z. Chen, L. Wei, J. Zhang, Org. Lett., 2011, 13, 1170; DOI: https://doi.org/10.1021/ol2000292.

    Article  CAS  PubMed  Google Scholar 

  31. E. K. Aminova, A. N. Kazakova, M. V. Proskurina, S. S. Zlotskii, Izv. VUZov. Khim. Khim. Tekhnol. [Bulletin of Higher Educational Institutions. Chem. Chem. Technol.], 2013, 56, 11 (in Russian).

    CAS  Google Scholar 

  32. M. T. Genta, C. Villa, E. Mariani, M. Longobardi, A. Loupy, Int. J. Cosmet. Sci., 2002, 24, 257; DOI: https://doi.org/10.1046/j.1467-2494.2002.00147.x13.

    Article  CAS  PubMed  Google Scholar 

  33. H. Flink, T. Putkonen, A. Sipos, R. Jokela, Tetrahedron, 2010, 66, 887; DOI: https://doi.org/10.1016/j.tet.2009.11.107.

    Article  CAS  Google Scholar 

  34. A. R. Makhmutov, Russ. J. Org. Chem., 2018, 54, 1710; DOI: https://doi.org/10.1134/S0514749218110146.

    Article  CAS  Google Scholar 

  35. Y. Du, F. Tian, Catal. Commun., 2007, 8, 2012; DOI: https://doi.org/10.1016/j.catcom.2007.03.021.

    Article  CAS  Google Scholar 

  36. S. Yamabe, T. Fukuda, S. Yamazaki, Beil. J. Org. Chem., 2013, 9, 476; DOI: https://doi.org/10.3762/bjoc.9.51.

    Article  CAS  Google Scholar 

  37. K. Alali, F. Lebsir, R. Hayder, A. Rahmouni, M. Kamoun, N. Besbes, Moroccan J. Heterocycl. Chem., 2022, 21, 27; DOI: https://doi.org/10.48369/IMIST.PRSM/jmch-v21i01.32986.

    CAS  Google Scholar 

  38. W. Harnying, J.-M. Neudörfl, Aerkessel, Synthesis, 2017, 49, 269; DOI: https://doi.org/10.1055/s-0036-1588367.

    Article  CAS  Google Scholar 

  39. M. Pastor, M. Yus, Curr. Org. Chem., 2012, 16, 1277; DOI: https://doi.org/10.2174/138527212800564196.

    Article  CAS  Google Scholar 

  40. S. Sreevardhan Reddy, B. David Raju, V. Siva Kumar, A. H. Padmasri, S. Narayanan, K. S. Rama Rao, Catal. Commun., 2007, 8, 261; DOI: https://doi.org/10.1016/j.catcom.2006.05.050.

    Article  Google Scholar 

  41. J. Wang, S. Jaenicke, G. K. Chuah, W. Hua, Y. Yue, Z. Gao, Catal. Commun., 2011, 12, 1131; DOI: https://doi.org/10.1016/j.catcom.2011.03.034.

    Article  CAS  Google Scholar 

  42. M. Pastor, M. Yus, Curr. Org. Chem., 2007, 11, 925; DOI: https://doi.org/10.2174/138527207781024067.

    Article  CAS  Google Scholar 

  43. I. S. Shepelevich, D. I. Gadzovskii, I. V. Vakulin, I. F. Talipov, Bash. Khim. Zh. [Bashkir Chem. J.], 2007, 14, 132 (in Russian).

    CAS  Google Scholar 

  44. S. P. Bedenko, K. I. Dement’ev, V. F. Tret’yakov, A. L. Maksimov, Petroleum Chem., 2020, 60, 723; DOI: https://doi.org/10.1134/S0965544120070026.

    Article  CAS  Google Scholar 

  45. M. Selvaraj, M. A. Assiri, H. Singh, J. N. Appaturi, C. Subrahmanyam, C.-S. Ha, Dalton Trans., 2021, 50, 1672; DOI: https://doi.org/10.1039/D0DT04158K.

    Article  CAS  PubMed  Google Scholar 

  46. H. Fu, S. Xie, A. Fu, T. Ye, Comput. Theor. Chem., 2012, 982, 51; DOI: https://doi.org/10.1016/j.comptc.2011.12.010.

    Article  CAS  Google Scholar 

  47. I. V. Vakulin, P. A. Pas’ko, R. F. Talipov, G. R. Talipova, O. Y. Kupova, Kinet. Catal. (Engl. Transl.), 2019, 60, 320; DOI: https://doi.org/10.1134/S045388111903016X.

    Article  CAS  Google Scholar 

  48. G. Rambabu, B. Palakshi Reddy, Y. B. Kiran, V. Vijayakumar, L. C. A. Barbosa, Res. Chem. Intermed., 2015, 41, 8441; DOI: https://doi.org/10.1007/s11164-014-1902-4.

    Article  CAS  Google Scholar 

  49. A. A. Hussein, H. S. Ali, J.Org. Chem., 2020, 85, 12682; DOI: https://doi.org/10.1021/acs.joc.0c01845.

    Article  CAS  PubMed  Google Scholar 

  50. S. Yang, Y. Zhang, X. Du, P. G. Merle, Rare Metals, 2008, 27, 89; DOI: https://doi.org/10.1016/S1001-0521(08)60037-6.

    Article  CAS  Google Scholar 

  51. V. R. Ruiz, A. Velty, L. L. Santos, A. Leyva-Pérez, M. J. Sabater, S. Iborra, A. Corma, J. Catal., 2010, 271, 351; DOI: https://doi.org/10.1016/j.jcat.2010.02.023.

    Article  CAS  Google Scholar 

  52. Y. K. Huang, L. Yu, G. B. Duan, Y. Z. Wang, M. B. Xu, S. J. Yang, Adv. Mater. Res., 2012, 531, 304; DOI: https://doi.org/10.4028/www.scientific.net/AMR.531.304.

    Article  CAS  Google Scholar 

  53. F. Guerrero-Ruíz, E. Yara-Varón, M. Dolores González, M. Torres, P. Salagre, R. Canela-Garayoa, Y. Cesteros, Fuel, 2022, 319, 123803; DOI: https://doi.org/10.1016/j.fuel.2022.123803.

    Article  Google Scholar 

  54. S. Krompiec, M. Penkala, K. Szczubiałka, E. Kowalska, Coord. Chem. Rev., 2012, 256, 2057; DOI: https://doi.org/10.1016/j.ccr.2012.05.006.

    Article  CAS  Google Scholar 

  55. D. Gorbunov, M. Nenasheva, A. Gorbunov, R. Matsukevich, A. Maximov, E. Karakhanov, Reaction Chem. Eng., 2021, 6, 839; DOI: https://doi.org/10.1039/D1RE00070E.

    Article  CAS  Google Scholar 

  56. S. Yu. Shavshukova, I. N. Vikhareva, E. A. Udalova, Bash. Khim. Zh. [Bashkir Chem. J.], 2009, 16, 123 (in Russian).

    Google Scholar 

  57. F. N. Latypova, F. Sh. Vil’danov, R. R. Chanyshev, S. S. Zlotskii, Izv. VUZov. Khim. Khim. Tekhnol. [Bulletin of Higher Educational Institutions. Chem. Chem. Technol.], 2015, 58, 3 (in Russian).

    CAS  Google Scholar 

  58. V. O. Samoilov, A. L. Maximov, T. I. Stolonogova, E. A. Chernysheva, V. M. Kapustin, A. O. Karpunina, Fuel, 2019, 249, 486–495; DOI: https://doi.org/10.1016/j.fuel.2019.02.098.

    Article  CAS  Google Scholar 

  59. K. Vanlaldinpuia, G. Bez, Tetrahedron Lett., 2011, 52, 3759; DOI:https://doi.org/10.1016/j.tetlet.2011.05.050.

    Article  CAS  Google Scholar 

  60. T. F. Dekhtyar’, O. S. Vostrikova, S. S. Zlotskii, A. A. Bogomazova, N. N. Mikhailova, Petroleum Chem., 2019, 59, 650; DOI: https://doi.org/10.1134/S0965544119060082.

    Article  Google Scholar 

  61. E. A. Yakovenko, Cand. Sci. (Chem.) Dissertation, Ufa State Peteroleum Technical University, Ufa, 2019, 130 pp. (in Russian).

    Google Scholar 

  62. O. A. Kolyamshin, Y. N. Mitrasov, V. A. Danilov, A. A. Avruiskaya, Y. Y. Pylchikova, N. P. Savinova, Russ. J. Gen. Chem., 2021, 91, 34; DOI: https://doi.org/10.1134/S1070363221010023.

    Article  CAS  Google Scholar 

  63. G. Z. Raskil’dina, Doct. Sci. (Chem.) Dissertation, Ufa State Peteroleum Technical University, Ufa, 2021, 310 pp. (in Russian).

    Google Scholar 

  64. V. F. Valiev, G. Z. Raskil’dina, S. S. Zlotskii, Russ. J. Appl. Chem., 2016, 89, 753; DOI: https://doi.org/10.1134/S1070427216050116.

    Article  Google Scholar 

  65. A. N. Kazakova, S. A. Timofeeva, Yu. M. Yumakaeva, A. F. Khairullina, S. S. Zlotskii, Bash. Khim. Zh. [Bashkir Chem. J.], 2010, 17, No. 4, 19 (in Russian).

    CAS  Google Scholar 

  66. V. M. Kotlov, S. S. Vershinin, O. A. Bondareva, V. V. Zorin, Bash. Khim. Zh. [Bashkir Chem. J.], 2009, 16, No. 4, 55 (in Russian).

    CAS  Google Scholar 

  67. E. R. Mindiyarova, S. S. Vershinin, V. V. Zorin, Bash. Khim. Zh. [Bashkir Chem. J.], 2014, 21, 13 (in Russian).

    CAS  Google Scholar 

  68. G. N. Sakhabutdinova, E. A. Yakovenko, G. Z. Raskil’dina, S. S. Zlotskii, Russ. J. Appl. Chem., 2020, 93, 967; DOI: https://doi.org/10.31857/S004446182007004X.

    Article  CAS  Google Scholar 

  69. G. Z. Raskil’dina, V. F. Valiev, R. M. Sultanova, S. S. Zlotskii, Russ. J. Appl. Chem., 2015, 88, 1599; DOI: 10.1134/S1070427215100079.

    Article  Google Scholar 

  70. E. A. Yakovenko, A. V. Baiburtli, Yu. G. Borisova, G. Z. Raskil’dina, Bash. Khim. Zh. [Bashkir Chem. J.], 2017, 24, No. 2, 52–56 (in Russian).

    CAS  Google Scholar 

  71. V. Polshettiwar, R. S. Varma, J. Org. Chem., 2007, 72, 7420; DOI: https://doi.org/10.1021/jo701337j.

    Article  CAS  PubMed  Google Scholar 

  72. A. I. Musin, Yu. G. Borisova, G. Z. Raskil’dina, R. R. Daminev, A. R. Davletshin, S. S. Zlotskii, Fine Chem. Technol., 2022, 17, 201; DOI: https://doi.org/10.32362/2410-6593-2022-17-3-201-209.

    Article  Google Scholar 

  73. S. A. Timofeeva, L. R. Yakupova, R. L. Safiullin, S. S. Zlotskii, Petroleum Chem., 2012, 52, 432; DOI: https://doi.org/10.1134/S096554411205012X.

    Article  CAS  Google Scholar 

  74. B. D. Mullen, V. Badarinarayana, M. Santos-Martinez, S. Selifonov, Top. Catal., 2010, 53, 1235; DOI: https://doi.org/10.1007/s11244-010-9585.

    Article  CAS  Google Scholar 

  75. US Pat. 2012157560-A1; PubChem, https://pubchem.ncbi.nlm.nih.gov.

  76. R. Alan Aitken, L. A. Power, Ch. 5.6–Five-membered ring systems: with O and S (Se, Te) atoms, in Progress in Heterocyclic Chemistry, Eds G. W. Gribble, J. A. Joule, Vol. 18, Elsevier, 2007, pp. 276–287.

  77. M. Hayakawa, H. Shirota, S. Hirayama, R. Yamada, T. Aoyama, A. Uchi, J. Photochem. Photobiol. A: Chemistry, 2021, 413, 113263; DOI: https://doi.org/10.1016/j.jphotochem.2021.113263.

    Article  CAS  Google Scholar 

  78. M. Hayakawa, R. Shimizu, H. Omori, H. Shirota, K. Uchida, H. Ashimo, H. Xu, R. Yamada, S. Niino, Y. Wakame, C. Liu, T. Aoyama, A. Ouchi, Tetrahedron, 2020, 76, 131557; DOI: https://doi.org/10.1016/j.tet.2020.131557.

    Article  CAS  Google Scholar 

  79. K. Yamada, M. Maekawa, T. Akindele, M. Nakano, Y. Yamamoto, K. Tomioka, J. Org. Chem., 2008, 73, 9535; DOI: https://doi.org/10.1021/jo801541m.

    Article  CAS  PubMed  Google Scholar 

  80. M. J. Porter, Synthesis, 2003, 2003, 1134; DOI: https://doi.org/10.1055/s-2003-39154.

    Article  Google Scholar 

  81. D. M. Hodgson, S. Man, K. J. Powell, Z. Perko, M. Zeng, E. Moreno-Clavijo, A. L. Thompson, M. D. Moore, J. Org. Chem., 2014, 79, 9728; DOI: https://doi.org/10.1021/jo501893r.

    Article  CAS  PubMed  Google Scholar 

  82. R. M. Sultanova, M. D. Khanova, V. A. Dokichev, ARKIVOC, 2009, 2009, 236; DOI: https://doi.org/10.3998/ark.5550190.0010.914.

    Article  Google Scholar 

  83. M. D. Khanova, R. M. Sultanova, V. A. Dokichev, S. S. Zlotskii, Dokl. Chem. (Engl. Transl.), 2007, 414, 106; DOI: https://doi.org/10.1134/S0012500807050023.

    CAS  Google Scholar 

  84. R. Ballesteros-Garrido, D. Rix, C. Besnard, J. Lacour, Chem.–Eur. J., 2012, 18, 6626; DOI: https://doi.org/10.1002/chem.201103870.

    Article  CAS  PubMed  Google Scholar 

  85. G. N. Shaikhullina, R. M. Sultanova, G. Z. Raskil’dina, S. S. Zlotskii, I. P. Baikova, Russ. Chem. Bull., 2017, 66, 164; DOI: https://doi.org/10.1007/s11172-017-1715-x.

    Article  CAS  Google Scholar 

  86. G. Z. Raskil’dina, S. S. Zlotsky, R. M. Sultanova, Macroheterocycles, 2018, 11, 166; DOI: https://doi.org/10.6060/mhc170622s.

    Article  Google Scholar 

  87. G. N. Sakhabutdinova, I. P. Baikova, G. Z. Raskil’dina, S. S. Zlotskii, R. M. Sultanova, Russ. J. Org. Chem., 2018, 54, 373; DOI: https://doi.org/10.1134/S1070428018030016.

    Article  CAS  Google Scholar 

  88. S. Muthusamy, J. Krishnamurthi, E. Suresh, Chem. Commun., 2007, 861; DOI: https://doi.org/10.1039/B613008A.

  89. I. Shcherbakova, Eight-membered Rings with Two Heteroatoms 1,4, in Comprehensive Heterocyclic Chemistry III, Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. Taylor, Vol. 14, Elsevier, 2008, 255 pp.; DOI: https://doi.org/10.1016/B978-808044992-0.01223-2.

  90. Germany Pat., DE19525314.

  91. α-Tertiary Amines en Route to Natural Products, Eds A. Hameed, M. Al-Rashida, M. R. Shah, Elsevier, 2021, p. iii; DOI: https://doi.org/10.1016/B978-0-12-822262-1.01001-5.

  92. P. H. R. Silva, V. L. C. Gonçalves, C. J. A. Mota, Biores. Technol., 2010, 101, 6225; DOI: https://doi.org/10.1016/j.biortech.2010.02.101.

    Article  CAS  Google Scholar 

  93. E. E. Falco, M. Patel, J. P. Fisher, Pharmaceut. Res., 2008, 25, 2348; DOI: https://doi.org/10.1007/s11095-008-9620-5.

    Article  CAS  Google Scholar 

  94. A. V. Mamlieva, N. N. Mikhailova, S. Yu. Shavshukova, NefteGazoKhimiya [Oil and Gas Chemistry], 2020, 30 (in Russian).

  95. Y.-J. Wu, N. A. Meanwell, J. Med. Chem., 2021, 64, 9786; DOI: https://doi.org/10.1021/acs.jmedchem.1c00790.

    Article  CAS  PubMed  Google Scholar 

  96. M. N. Ovsyannikova, V. B. Vol’eva, I. S. Belostotskaya, N. L. Komissarova, A. V. Malkova, L. N. Kurkovskaya, Pharm. Chem. J. (Engl.Trans.), 2013, 47, 132; DOI https://doi.org/10.30906/0023-1134-2013-47-3-18-21.

    Google Scholar 

Download references

Funding

This work was financially supported by the state assignment of the Ministry of Science and Higher Education of the Russian Federation “Development and Production of Low-Tonnage Products and Reagents (Corrosion and Scale Inhibitors, Anti-oxidants, Biocides, Additives, and Others) for Processes of Oil and Gas Chemistry and Aqueous Media Decontamination from Impurities Substituting Imported Substances and Materials. Theoretical and Experimental Approaches (FEUR-2023-0006).”

Author information

Authors and Affiliations

  1. Ufa State Petroleum Technological University, 1 ul. Kosmonavtov, 450064, Ufa, Russian Federation

    R. M. Sultanova, Yu. G. Borisova, N. S. Khusnutdinova, G. Z. Raskil’dina & S. S. Zlotskii

Authors
  1. R. M. Sultanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. G. Borisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. S. Khusnutdinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. Z. Raskil’dina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. S. Zlotskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. M. Sultanova.

Ethics declarations

Animal Testing and Ethics

No human or animal subjects were used in this research.

Conflict of Interest

The authors declare no competing interests.

Additional information

Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2297–2318, October, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sultanova, R.M., Borisova, Y.G., Khusnutdinova, N.S. et al. 1,3-Dioxacyclanes: synthesis based on petrochemicals, chemical transformations, and applications. Russ Chem Bull 72, 2297–2318 (2023). https://doi.org/10.1007/s11172-023-4027-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-4027-3

Key words

Search

Navigation