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 <front>
  <journal-meta>
   <journal-id journal-id-type="publisher-id">From Chemistry Towards Technology Step-By-Step</journal-id>
   <journal-title-group>
    <journal-title xml:lang="en">From Chemistry Towards Technology Step-By-Step</journal-title>
    <trans-title-group xml:lang="ru">
     <trans-title>От химии к технологии шаг за шагом</trans-title>
    </trans-title-group>
   </journal-title-group>
   <issn publication-format="online">2782-1900</issn>
  </journal-meta>
  <article-meta>
   <article-id pub-id-type="publisher-id">81126</article-id>
   <article-id pub-id-type="doi">10.52957/2782-1900-2024-4-4-82-88</article-id>
   <article-categories>
    <subj-group subj-group-type="toc-heading" xml:lang="ru">
     <subject>Научные статьи</subject>
    </subj-group>
    <subj-group subj-group-type="toc-heading" xml:lang="en">
     <subject>Scientific articles</subject>
    </subj-group>
    <subj-group>
     <subject>Научные статьи</subject>
    </subj-group>
   </article-categories>
   <title-group>
    <article-title xml:lang="en">Synthesis of N-substituted heterocycles in a sealed Monowave 50 reactor</article-title>
    <trans-title-group xml:lang="ru">
     <trans-title>Синтез N-замещенных гетероциклов в герметичном реакторе Monowave 50</trans-title>
    </trans-title-group>
   </title-group>
   <contrib-group content-type="authors">
    <contrib contrib-type="author">
     <name-alternatives>
      <name xml:lang="ru">
       <surname>Савина</surname>
       <given-names>Луиза Ильинична</given-names>
      </name>
      <name xml:lang="en">
       <surname>Savina</surname>
       <given-names>Luisa Ilyinichna</given-names>
      </name>
     </name-alternatives>
     <email>luizasavina2000@mail.ru</email>
     <xref ref-type="aff" rid="aff-1"/>
     <xref ref-type="aff" rid="aff-2"/>
    </contrib>
    <contrib contrib-type="author">
     <name-alternatives>
      <name xml:lang="ru">
       <surname>Соколов</surname>
       <given-names>Александр Андреевич</given-names>
      </name>
      <name xml:lang="en">
       <surname>Sokolov</surname>
       <given-names>Aleksandr Andreevich</given-names>
      </name>
     </name-alternatives>
     <xref ref-type="aff" rid="aff-3"/>
    </contrib>
   </contrib-group>
   <aff-alternatives id="aff-1">
    <aff>
     <institution xml:lang="ru">Ярославский государственный медицинский университет</institution>
    </aff>
    <aff>
     <institution xml:lang="en">Yaroslavl State Medical University</institution>
    </aff>
   </aff-alternatives>
   <aff-alternatives id="aff-2">
    <aff>
     <institution xml:lang="ru">Ярославский государственный университет им. П.Г. Демидова</institution>
    </aff>
    <aff>
     <institution xml:lang="en">P.G. Demidov Yaroslavl State University</institution>
    </aff>
   </aff-alternatives>
   <aff-alternatives id="aff-3">
    <aff>
     <institution xml:lang="ru">Ярославский государственный технический университет</institution>
    </aff>
    <aff>
     <institution xml:lang="en">Yaroslavl State Technical University</institution>
    </aff>
   </aff-alternatives>
   <pub-date publication-format="print" date-type="pub" iso-8601-date="2023-12-23T00:00:00+03:00">
    <day>23</day>
    <month>12</month>
    <year>2023</year>
   </pub-date>
   <pub-date publication-format="electronic" date-type="pub" iso-8601-date="2023-12-23T00:00:00+03:00">
    <day>23</day>
    <month>12</month>
    <year>2023</year>
   </pub-date>
   <volume>4</volume>
   <issue>4</issue>
   <fpage>82</fpage>
   <lpage>88</lpage>
   <history>
    <date date-type="received" iso-8601-date="2023-10-28T00:00:00+03:00">
     <day>28</day>
     <month>10</month>
     <year>2023</year>
    </date>
    <date date-type="accepted" iso-8601-date="2023-11-15T00:00:00+03:00">
     <day>15</day>
     <month>11</month>
     <year>2023</year>
    </date>
   </history>
   <self-uri xlink:href="https://chemintech.ru/en/nauka/article/81126/view">https://chemintech.ru/en/nauka/article/81126/view</self-uri>
   <abstract xml:lang="ru">
    <p>Осуществлён процесс ароматического нуклеофильного замещения в 2-хлорнитробензоле и 2,4-дихлор-1,5-динитробензоле в реакторе для синтеза Monowave 50. Установлено ускорение реакций субстратов с азагетероциклическими соединениями (пиридином или индолом) в герметично закрытых сосудах.</p>
   </abstract>
   <trans-abstract xml:lang="en">
    <p>The paper examines the process of aromatic nucleophilic substitution in 2-chloronitrobenzene and 2,4-dichloro-1,5-dinitrobenzene in a Monowave 50 synthesis reactor. The authors identify accelerated reactions of substrates with azaheterocyclic compounds (pyridine or indole) in hermetically sealed vessels.</p>
   </trans-abstract>
   <kwd-group xml:lang="ru">
    <kwd>2-хлорнитробензол</kwd>
    <kwd>2</kwd>
    <kwd>4-дихлор-1</kwd>
    <kwd>5-динитробензол</kwd>
    <kwd>азагетероциклы</kwd>
    <kwd>реактор Monowave 50</kwd>
    <kwd>ароматическое нуклеофильное замещение</kwd>
   </kwd-group>
   <kwd-group xml:lang="en">
    <kwd>2-chloronitrobenzene</kwd>
    <kwd>2</kwd>
    <kwd>4-dichloro-1</kwd>
    <kwd>5-dinitrobenzene</kwd>
    <kwd>azaheterocycles</kwd>
    <kwd>Monowave 50 reactor</kwd>
    <kwd>aromatic nucleophilic substitution</kwd>
   </kwd-group>
  </article-meta>
 </front>
 <body>
  <p></p>
 </body>
 <back>
  <ref-list>
   <ref id="B1">
    <label>1.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Xu H., Liu W.-Q., Fan L.-L., Chen Y., Yang L.-M., Lv L., Zheng Y.-T. Synthesis and HIV-1 Integrase Inhibition Activity of some N-Arylindoles // Chem. Pharm. Bull. 2008. Vol. 56, iss. 5. P. 720-722. DOI: 10.1248/cpb.56.720. URL: https://www.jstage.jst.go.jp/article/cpb/56/5/56_5_720/_article</mixed-citation>
     <mixed-citation xml:lang="en">Xu, H., Liu, W.-Q., Fan, L.-L., Chen, Y., Yang, L.-M., Lv, L. &amp; Zheng, Y.-T. (2008) Synthesis and HIV-1 Integrase Inhibition Activity of some N-Arylindoles, Chem. Pharm. Bull., 56(5), pp. 720-722. DOI: 10.1248/cpb.56.720 [online]. Available at: https://www.jstage.jst.go.jp/article/cpb/56/5/56_5_720/_article (accessed 20.08.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B2">
    <label>2.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Desplat V., Moreau S., Belisle-Fabre S., Thiolat D., Uranga J., Lucas R., de Moor L., Massip S., Jarry C., Mossalayi D.M., Sonnet P., Deleris G., Guillon J. Synthesis and evaluation of the antiproliferative activity of novel isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives // J. Enzyme Inhib. Med. Chem. 2011. Vol. 26(5). P. 657-667. DOI: 10.3109/14756366.2010.548326. URL: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.548326</mixed-citation>
     <mixed-citation xml:lang="en">Desplat, V., Moreau, S., Belisle-Fabre, S., Thiolat, D., Uranga, J., Lucas, R., de Moor, L., Massip, S., Jarry, C., Mossalayi, D.M., Sonnet, P., Deleris, G. &amp; Guillon, J. (2011) Synthesis and evaluation of the antiproliferative activity of novel isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives, J. Enzyme Inhib. Med. Chem., 26(5), pp. 657-667. DOI: 10.3109/14756366.2010.548326 [online]. Available at:  https://www.tandfonline.com/doi/full/10.3109/14756366.2010.548326 (accessed 20.09.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B3">
    <label>3.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Xu H., Fan L-L. Antifungal agents. Part 4: Synthesis and antifungal activities of novel indole[1,2-c]-1,2,4-benzotriazine derivatives against phytopathogenic fungi in vitro // Eur. J. Med. Chem. 2011. Vol. 46(1). P. 364-369. DOI: 10.1016/j.ejmech.2010.10.022. URL: https://www.sciencedirect.com/science/article/abs/pii/S0223523410007622</mixed-citation>
     <mixed-citation xml:lang="en">Xu, H. &amp; Fan, L-L. (2011) Antifungal agents. Part 4: Synthesis and antifungal activities of novel indole[1,2-c]-1,2,4-benzotriazine derivatives against phytopathogenic fungi in vitro, Eur. J. Med. Chem., 46(1), pp. 364-369. DOI: 10.1016/j.ejmech.2010.10.022 [online]. Available at:  https://www.sciencedirect.com/science/article/abs/pii/S0223523410007622  (accessed 20.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B4">
    <label>4.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Yan Y., Liu Z., Zhang J., Xu R., Hu X., Liu G. A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors // Bioorganic Med. Chem. Lett. 2011. Vol. 21(14). P. 4189-4192. DOI: 10.1016/j.bmcl.2011.05.080. URL: https://www.sciencedirect.com/science/article/pii/S0960894X11007098</mixed-citation>
     <mixed-citation xml:lang="en">Yan, Y., Liu, Z., Zhang, J., Xu, R., Hu, X. &amp; Liu, G. (2011) A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors, Bioorganic Med. Chem. Lett., 21(14), pp. 4189 4192. DOI: 10.1016/j.bmcl.2011.05.080 [online]. Available at:  https://www.sciencedirect.com/science/article/pii/S0960894X11007098 (accessed 20.08.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B5">
    <label>5.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Tokay E., Güngör T., Hacıoğlu N., Önder F.C., Gülhan Ü.G., Tok T.T., Çelik A., Ay M., Köçkar F. Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer // Eur. J. Med. Chem. 2020. Vol. 187. P. 111937-111957. DOI: 10.1016/j.ejmech.2019.111937. URL: https://www.sciencedirect.com/science/article/pii/S022352341931089X</mixed-citation>
     <mixed-citation xml:lang="en">Tokay, E., Güngör,T., Hacıoğlu, N., Önder, F.C., Gülhan, Ü.G., Tok, T.T., Çelik, A., Ay, M. &amp; Köçkar, F. (2020) Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer, Eur. J. Med. Chem., 187, pp. 111937-111957. DOI: 10.1016/j.ejmech.2019.111937. Available at: https://www.sciencedirect.com/science/article/pii/S022352341931089X (accessed 23.08.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B6">
    <label>6.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Kumar K., Awasthi D., Lee S.-Y., Cummings J.E., Knudson S.E., Slayden R.A., Ojima I. Benzimidazole-based antibacterial agents against // Francisella tularensis // Bioorganic Med. Chem. 2013. Vol. 21, iss. 11. P. 3318-3326. DOI: 10.1016/j.bmc.2013.02.059. URL: https://www.sciencedirect.com/science/article/pii/S0968089613002605</mixed-citation>
     <mixed-citation xml:lang="en">Kumar, K., Awasthi, D., Lee, S.-Y., Cummings, J.E., Knudson, S.E., Slayden, R.A. &amp; Ojima, I. (2013) Benzimidazole-based antibacterial agents against, Francisella tularensis. Bioorganic Med. Chem., 21(11), pp. 3318-3326. DOI: 10.1016/j.bmc.2013.02.059 [online]. Available at: https://www.sciencedirect.com/science/article/pii/S0968089613002605 (accessed 20.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B7">
    <label>7.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Kumar K., Awasthi D., Lee S.-Y., Zanardi I., Ruzsicska B., Knudson S., Tonge P.J., Slayden R.A., Ojima I. Novel Trisubstituted Benzimidazoles, Targeting Mtb FtsZ, as a New Class of Antitubercular Agents // J. Med. Chem. 2011. Vol. 54(1). P. 374-381. DOI: 10.1021/jm1012006. URL: https://pubs.acs.org/doi/10.1021/jm1012006</mixed-citation>
     <mixed-citation xml:lang="en">Kumar, K., Awasthi, D., Lee, S.-Y., Zanardi, I., Ruzsicska, B., Knudson, S., Tonge, P.J., Slayden, R.A. &amp; Ojima, I. (2011) Novel Trisubstituted Benzimidazoles, Targeting Mtb FtsZ, as a New Class of Antitubercular Agents, J. Med. Chem., 54(1), pp. 374-381. DOI: 10.1021/jm1012006 [online]. Available at:  https://pubs.acs.org/doi/10.1021/jm1012006 (accessed 20.08.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B8">
    <label>8.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Awasthi D., Kumar K., Knudson S., Slayden R.A., Ojima I. SAR Studies on TrisubstitutedBenzimidazoles as Inhibitors of Mtb FtsZ for the Development of Novel Antitubercular Agents // J. Med. Chem. 2013. Vol. 56(23). P. 9756-9770. DOI: 10.1021/jm401468w. URL: https://pubs.acs.org/doi/10.1021/jm401468w</mixed-citation>
     <mixed-citation xml:lang="en">Awasthi, D., Kumar, K., Knudson, S., Slayden, R.A. &amp; Ojima, I. (2013) SAR Studies on TrisubstitutedBenzimidazoles as Inhibitors of Mtb FtsZ for the Development of Novel Antitubercular Agents, J. Med. Chem., 56(23), pp. 9756-9770. DOI: 10.1021/jm401468w [online]. Available at:  https://pubs.acs.org/doi/10.1021/jm401468w (accessed 20.07.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B9">
    <label>9.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Gong Y., Karakaya S.S., Guo X., Zheng P., Gold B., Ma Y., Little D., Roberts J., Warrier T., Jiang X., Pingle M., Nathan C.F., Liu G. Benzimidazole-based compounds kill Mycobacterium tuberculosis // Eur. J. Med. Chem. 2014. Vol. 75. P. 336-353. DOI: 10.1016/j.ejmech.2014.01.039. URL: https://www.sciencedirect.com/science/article/pii/S0223523414000853</mixed-citation>
     <mixed-citation xml:lang="en">Gong, Y., Karakaya, S.S., Guo, X., Zheng, P., Gold, B., Ma, Y., Little, D., Roberts, J., Warrier, T., Jiang, X., Pingle, M., Nathan, C.F. &amp; Liu, G. (2014) Benzimidazole-based compounds kill Mycobacterium tuberculosis // Eur. J. Med. Chem., 75, pp. 336-353. DOI: 10.1016/j.ejmech.2014.01.039 [online]. Available at: https://www.sciencedirect.com/science/article/pii/S0223523414000853 (accessed 20.08.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B10">
    <label>10.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Zhong Q.-F., Liu R., Liu G. Structure–activity relationship studies on quinoxalin-2(1H)-one derivatives containing thiazol-2-amine against hepatitis C virus leading to the discovery of BH6870 // Mol. Divers. 2015. Vol. 19(4). P. 829 853. DOI: 10.1007/s11030-015-9610-6. URL: https://link.springer.com/article/10.1007/s11030-015-9610-6</mixed-citation>
     <mixed-citation xml:lang="en">Zhong, Q.-F., Liu, R. &amp; Liu, G. (2015) Structure–activity relationship studies on quinoxalin-2(1H)-one derivatives containing thiazol-2-amine against hepatitis C virus leading to the discovery of BH6870, Mol. Divers., 19(4), pp. 829-853. DOI: 10.1007/s11030-015-9610-6 [online]. Available at: https://link.springer.com/article/10.1007/s11030-015-9610-6 (accessed 20.08.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B11">
    <label>11.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Patent N 2011/0257146 A1 US. Method of treating KCNQ related disorders using organozinc compounds / Li M., Sun H., Xiong Q. Publ. 2011. URL: https://patents.google.com/patent/US20110257146A1/en</mixed-citation>
     <mixed-citation xml:lang="en">Li, M., Sun, H. &amp; Xiong, Q. (2011) Method of treating KCNQ related disorders using organozinc compounds. 2011/0257146 A1 US.</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B12">
    <label>12.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Ibata T., Isogami Y., Toyoda J. Aromatic Nucleophilic Substitution of Halobenzenes with Amines under High Pressure // Bull. Chem. Soc. Jpn. 1991. Vol. 64(1). P. 42-49. DOI: 10.1246/bcsj.64.42. URL: https://www.journal.csj.jp/doi/10.1246/bcsj.64.42</mixed-citation>
     <mixed-citation xml:lang="en">Ibata, T., Isogami, Y. &amp; Toyoda, J. (1991) Aromatic Nucleophilic Substitution of Halobenzenes with Amines under High Pressure, Bull. Chem. Soc. Jpn., 64(1), pp. 42-49. DOI: 10.1246/bcsj.64.42 [online]. Available at: https://www.journal.csj.jp/doi/10.1246/bcsj.64.42 (accessed 20.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B13">
    <label>13.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Lengyel L., Gyóllai V., Nagy T., Dormán G., Terleczky P., Háda V., Nógrádi K., Sebők F., Ürge L., Darvas F. Stepwise aromatic nucleophilic substitution in continuous flow. Synthesis of an unsymmetrically substituted 3,5-diamino-benzonitrile library // Mol. Divers. 2011. Vol. 15(3). P. 631-638. DOI: 10.1007/s11030-010-9300-3. URL: https://link.springer.com/article/10.1007/s11030-010-9300-3</mixed-citation>
     <mixed-citation xml:lang="en">Lengyel, L., Gyóllai, V., Nagy, T., Dormán, G., Terleczky, P., Háda, V., Nógrádi, K., Sebők, F., Ürge, L. &amp; Darvas, F. (2011) Stepwise aromatic nucleophilic substitution in continuous flow. Synthesis of an unsymmetrically substituted 3,5-diamino-benzonitrile library, Mol. Divers., 15(3), pp. 631-638. DOI: 10.1007/s11030-010-9300-3 [online].  Available at:  https://link.springer.com/article/10.1007/s11030-010-9300-3 (accessed 20.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B14">
    <label>14.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Petersen T.P., Larsen A.F., Ritzen A., Ulven T. Continuous Flow Nucleophilic Aromatic Substitution with Dimethylamine Generated in Situ by Decomposition of DMF // J. Org. Chem. 2013. Vol. 78(8). P. 4190-4195. DOI: 10.1021/jo400390t. URL: https://pubs.acs.org/doi/10.1021/jo400390t</mixed-citation>
     <mixed-citation xml:lang="en">Petersen, T.P., Larsen, A.F., Ritzen, A. &amp; Ulven, T. (2013) Continuous Flow Nucleophilic Aromatic Substitution with Dimethylamine Generated in Situ by Decomposition of DMF, J. Org. Chem., 78(8), pp. 4190 4195. DOI: 10.1021/jo400390t [online]. Available at: https://pubs.acs.org/doi/10.1021/jo400390t (accessed 10.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B15">
    <label>15.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Kocienski P. Conductively Heated Sealed-Vessel Reactor: Synthesis of Olanzapine // Synfacts. 2017. Vol. 13(03). P. 0231. DOI: 10.1055/s-0036-1590077. URL: https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1590077</mixed-citation>
     <mixed-citation xml:lang="en">Kocienski, P. (2017) Conductively Heated Sealed-Vessel Reactor: Synthesis of Olanzapine, Synfacts, 13(03), pp. 0231. DOI: 10.1055/s-0036-1590077 [online]. Available at: https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1590077 (accessed 10.09.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B16">
    <label>16.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Synthesis reactor: Monowave 50 // Anton Paar: [site]. URL: https://www.anton-paar.com/corp-en/products/details/synthesis-reactor-monowave-50/</mixed-citation>
     <mixed-citation xml:lang="en">Anton Paar. (2023) Synthesis reactor: Monowave 50 [online]. Available at: https://www.anton-paar.com/corp-en/products/details/synthesis-reactor-monowave-50/ (accessed 20.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B17">
    <label>17.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Abramov I.G., Baklagin V.L., Makarova E.S., Kleikova D.E. Nitrogen-containing heterocyclic O-, and S-nucleophiles in reactions with 4-nitrophthalonitrile and 4-bromo-5-nitrophthalonitrile // From Chemistry Towards Technology Step-Вy-Step. 2021. Vol. 2, no. 4. P. 93-99. DOI: 10.52957/27821900_2021_04_93. URL: http://chemintech.ru/index.php/tor/2021-2-4</mixed-citation>
     <mixed-citation xml:lang="en">Abramov, I.G., Baklagin, V.L., Makarova, E.S. &amp; Kleikova, D.E. (2021) Nitrogen-containing heterocyclic O , and S-nucleophiles in reactions with 4-nitrophthalonitrile and 4-bromo-5-nitrophthalonitrile, From Chemistry Towards Technology Step-By-Step, 2(4), pp. 93-99. DOI: 10.52957/27821900_2021_04_93 [online]. Available at: http://chemintech.ru/index.php/tor/2021-2-4 (accessed 20.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B18">
    <label>18.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Vitaku E., Smith D.T., Njardarson J.T. Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals // J. Med. Chem. 2014. Vol. 57, iss. 24. P. 10257-10274. DOI: 10.1021/jm501100b. URL: https://pubs.acs.org/doi/10.1021/jm501100b</mixed-citation>
     <mixed-citation xml:lang="en">Vitaku, E., Smith, D.T. &amp; Njardarson, J.T. (2014) Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals, J. Med. Chem., 57(24), pp. 10257-10274. DOI: 10.1021/jm501100b [online]. Available at: https://pubs.acs.org/doi/10.1021/jm501100b (accessed 20.10.2023).</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B19">
    <label>19.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Begunov R.S., Sokolov A.A., Filimonov S.I. Synthesis of Quinone Derivatives of Benzannelated Heterocycles with Bridgehead Nitrogen // Rus. J. Org. Chem. 2020. Vol. 56. P. 1383-1391. DOI: 10.1134/S1070428020080084. URL: https://link.springer.com/article/10.1134/S1070428020080084</mixed-citation>
     <mixed-citation xml:lang="en">Begunov R.S., Sokolov A.A., Filimonov S.I. Synthesis of Quinone Derivatives of Benzannelated Heterocycles with Bridgehead Nitrogen // Rus. J. Org. Chem. 2020. Vol. 56. P. 1383-1391. DOI: 10.1134/S1070428020080084. URL: https://link.springer.com/article/10.1134/S1070428020080084</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B20">
    <label>20.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Begunov R.S., ZaitsevaYu.V., Sokolov A.A., Egorov D.O., Filimonov S.I. Synthesis and Antibacterial Activity of 1,2,3,4-Tetrahydro- and Pyrido[1,2-a]Benzimidazoles // Pharm. Chem. J. 2022. Vol. 56, no. 1. P. 22 28. DOI: 10.1007/s11094-022-02596-0. URL: https://link.springer.com/article/10.1007/s11094-022-02596-0</mixed-citation>
     <mixed-citation xml:lang="en">Begunov R.S., ZaitsevaYu.V., Sokolov A.A., Egorov D.O., Filimonov S.I. Synthesis and Antibacterial Activity of 1,2,3,4-Tetrahydro- and Pyrido[1,2-a]Benzimidazoles // Pharm. Chem. J. 2022. Vol. 56, no. 1. P. 22 28. DOI: 10.1007/s11094-022-02596-0. URL: https://link.springer.com/article/10.1007/s11094-022-02596-0</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B21">
    <label>21.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Kumar S., Ritika. A brief review of the biological potential of indole derivatives // Future Journal of Pharmaceutical Sciences. 2020. Vol. 6. P. 121-140. DOI: 10.1186/s43094-020-00141-y. URL: https://fjps.springeropen.com/articles/10.1186/s43094-020-00141-y</mixed-citation>
     <mixed-citation xml:lang="en">Kumar S., Ritika. A brief review of the biological potential of indole derivatives // Future Journal of Pharmaceutical Sciences. 2020. Vol. 6. P. 121-140. DOI: 10.1186/s43094-020-00141-y. URL: https://fjps.springeropen.com/articles/10.1186/s43094-020-00141-y</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B22">
    <label>22.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Teraiya N., Agrawal K., Patel T.M., Patel A., Patel S., Shah U., Shah S., Rathod K., Patel K. A Review of the Therapeutic Importance of Indole Scaffold in Drug Discovery // Current Drug Discovery Technologies. 2023. Vol. 20(6). Article ID: e050523216584. DOI: 10.2174/1570163820666230505120553. URL: https://www.eurekaselect.com/article/131536</mixed-citation>
     <mixed-citation xml:lang="en">Teraiya N., Agrawal K., Patel T.M., Patel A., Patel S., Shah U., Shah S., Rathod K., Patel K. A Review of the Therapeutic Importance of Indole Scaffold in Drug Discovery // Current Drug Discovery Technologies. 2023. Vol. 20(6). Article ID: e050523216584. DOI: 10.2174/1570163820666230505120553. URL: https://www.eurekaselect.com/article/131536</mixed-citation>
    </citation-alternatives>
   </ref>
   <ref id="B23">
    <label>23.</label>
    <citation-alternatives>
     <mixed-citation xml:lang="ru">Badigenchala S., Rajechkumar V., Sekar G. A Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles // Org. Biomol. Chem. 2016. Vol. 14(7). P. 2297-2305. DOI: 10.1039/C5OB02449H. URL: https://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02449h</mixed-citation>
     <mixed-citation xml:lang="en">Badigenchala S., Rajechkumar V., Sekar G. A Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles // Org. Biomol. Chem. 2016. Vol. 14(7). P. 2297-2305. DOI: 10.1039/C5OB02449H. URL: https://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02449h</mixed-citation>
    </citation-alternatives>
   </ref>
  </ref-list>
 </back>
</article>
