<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE article PUBLIC "-//NLM//DTD JATS (Z39.96) Journal Publishing DTD v1.3 20210610//EN" "JATS-journalpublishing1-3.dtd">
<article article-type="research-article" dtd-version="1.3" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xml:lang="ru"><front><journal-meta><journal-id journal-id-type="publisher-id">dan</journal-id><journal-title-group><journal-title xml:lang="ru">Доклады Национальной академии наук Беларуси</journal-title><trans-title-group xml:lang="en"><trans-title>Doklady of the National Academy of Sciences of Belarus</trans-title></trans-title-group></journal-title-group><issn pub-type="ppub">1561-8323</issn><issn pub-type="epub">2524-2431</issn><publisher><publisher-name>The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="doi">10.29235/1561-8323-2020-64-4-426-430</article-id><article-id custom-type="elpub" pub-id-type="custom">dan-899</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="ru"><subject>ХИМИЯ</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="en"><subject>CHEMISTRY</subject></subj-group></article-categories><title-group><article-title>Получение хиральных изобензофуранов на основе 3-карена в присутствии галлуазитовых нанокатализаторов</article-title><trans-title-group xml:lang="en"><trans-title>Preparation of chiral izobenzofuranes based on 3-carene in the presence of halloysite nanocatalysts</trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Сидоренко</surname><given-names>А. Ю.</given-names></name><name name-style="western" xml:lang="en"><surname>Sidorenko</surname><given-names>A. Yu.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Сидоренко Александр Юрьевич - кандидат химических наук, заведующий лабораторией, ИХНМ НАН Беларуси.</p><p>ул. Скорины, 36, 220141, Минск.</p></bio><bio xml:lang="en"><p>Sidorenko Alexander Yu. - Ph. D. (Chemistry), Head of the Laboratory, Institute of Chemistry of New Materials of the National Academy of Sciences of Belarus.</p><p>36, Skorina Str., 220141, Minsk.</p></bio><email xlink:type="simple">sidorenko@ichnm.basnet.by</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Агабеков</surname><given-names>В. Е.</given-names></name><name name-style="western" xml:lang="en"><surname>Agabekov</surname><given-names>V. E.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Агабеков Владимир Енокович - академик, доктор химических наук, профессор, директор, ИХНМ НАН Беларуси.</p><p>ул. Скорины, 36, 220141, Минск.</p></bio><bio xml:lang="en"><p>Agabekov Vladimir E. - Academician, D. Sc. (Chemistry), Professor, Director, Institute of Chemistry of New Materials of the National Academy of Sciences of Belarus.</p><p>36, Skorina Str., 220141, Minsk.</p></bio><email xlink:type="simple">mixa@ichnm.basnet.by</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Волчо</surname><given-names>К. П.</given-names></name><name name-style="western" xml:lang="en"><surname>Volcho</surname><given-names>K. P.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Волчо Константин Петрович - доктор химических наук, профессор, главный научный сотрудник, НИОХ СО РАН им. Н.Н. Ворожцова.</p><p>пр. Академика Лаврентьева, 9, 630090, Новосибирск.</p></bio><bio xml:lang="en"><p>Volcho Konstantin P. - D. Sc. (Chemistry), Professor, Chief researcher, Novosibirsk Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences.</p><p>9, Lavrentiev Ave., 630090, Novosibirsk.</p></bio><email xlink:type="simple">volcho@nioch.nsc.ru</email><xref ref-type="aff" rid="aff-2"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Салахутдинов</surname><given-names>Н. Ф.</given-names></name><name name-style="western" xml:lang="en"><surname>Salakhutdinov</surname><given-names>N. F.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Салахутдинов Нариман Фаридович - член-корреспондент, доктор химических наук, профессор, руководитель отдела, НИОХ СО РАН им. Н.Н. Ворожцова.</p><p>пр. Академика Лаврентьева, 9, 630090, Новосибирск.</p></bio><bio xml:lang="en"><p>Salakhutdinov Nariman F. - Corresponding Member, D. Sc. (Chemistry), Professor, Head of the Department, Novosibirsk Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences.</p><p>9, Lavrentiev Ave., 630090, Novosibirsk.</p></bio><email xlink:type="simple">anvar@nioch.nsc.ru</email><xref ref-type="aff" rid="aff-2"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Мурзин</surname><given-names>Д. Ю.</given-names></name><name name-style="western" xml:lang="en"><surname>Murzin</surname><given-names>D. Yu.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Мурзин Дмитрий Юрьевич - доктор химических наук, профессор, заведующий лабораторией, Университет Або Академи.</p><p>Biskopsgatan 8, Turku-Abo, 20500.</p></bio><bio xml:lang="en"><p>Murzin Dmitry Yu. - D. Sc. (Chemistry), Professor, Head of the Laboratory, Abo Akademi University.</p><p>Biskopsgatan 8, Turku-Abo, 20500.</p></bio><email xlink:type="simple">dmurzin@abo.fi</email><xref ref-type="aff" rid="aff-3"/></contrib></contrib-group><aff-alternatives id="aff-1"><aff xml:lang="ru"><institution>Институт химии новых материалов Национальной академии наук Беларуси</institution></aff><aff xml:lang="en"><institution>Institute of Chemistry of New Materials of the National Academy of Sciences of Belarus</institution></aff></aff-alternatives><aff-alternatives id="aff-2"><aff xml:lang="ru"><institution>Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук</institution></aff><aff xml:lang="en"><institution>Novosibirsk Institute of Organic Chemistry of Siberian Branch of the Russian Academy of Sciences</institution></aff></aff-alternatives><aff-alternatives id="aff-3"><aff xml:lang="ru"><institution>Университет Або Академи</institution></aff><aff xml:lang="en"><institution>Abo Akademi University</institution></aff></aff-alternatives><pub-date pub-type="collection"><year>2020</year></pub-date><pub-date pub-type="epub"><day>30</day><month>08</month><year>2020</year></pub-date><volume>64</volume><issue>4</issue><fpage>426</fpage><lpage>430</lpage><permissions><copyright-statement>Copyright &amp;#x00A9; Сидоренко А.Ю., Агабеков В.Е., Волчо К.П., Салахутдинов Н.Ф., Мурзин Д.Ю., 2020</copyright-statement><copyright-year>2020</copyright-year><copyright-holder xml:lang="ru">Сидоренко А.Ю., Агабеков В.Е., Волчо К.П., Салахутдинов Н.Ф., Мурзин Д.Ю.</copyright-holder><copyright-holder xml:lang="en">Sidorenko A.Y., Agabekov V.E., Volcho K.P., Salakhutdinov N.F., Murzin D.Y.</copyright-holder><license xml:lang="ru" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>Данная работа распространяется под лицензией Creative Commons Attribution 4.0.</license-p></license><license xml:lang="en" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>This work is licensed under a Creative Commons Attribution 4.0 License.</license-p></license></permissions><self-uri xlink:href="https://doklady.belnauka.by/jour/article/view/899">https://doklady.belnauka.by/jour/article/view/899</self-uri><abstract><p>Исследовано взаимодействие содержащих 2-карен продуктов изомеризации 3-карена с 4-метокси-бензальдегидом в присутствии обработанных 5,0 % HCl галлуазитовых нанотрубок. Основными продуктами реакции являются хиральные производные изобензофурана. Селективность по этим соединениям (71,4 %) сопоставима с таковой при использовании труднодоступного индивидуального 2-карена. Показана возможность использования галлуазитовых нанокатализаторов для селективного получения изобензофурановых соединений на основе продуктов изомеризации 3-карена (компонента живичного скипидара) без предварительного разделения смеси.</p></abstract><trans-abstract xml:lang="en"><p>The reaction of a 2-carene containing mixture, obtained by 3-carene isomerization, with 4-methoxybenzalde-hyde in the presence of halloysite nanotubes treated with 5.0 % HCl was studied. The main reaction products are the chiral derivatives of isobenzofuran. Selectivity to these compounds (71.4 %) is comparable to that when only 2-carene is used as a reactant. Thus, the possibility is shown how to use halloysite nanocatalysts for selective production of isobenzofuran compounds based on 3-carene isomerization products (major component of turpentine) without preliminary mixture separation.</p></trans-abstract><kwd-group xml:lang="ru"><kwd>3-карен</kwd><kwd>галлуазитовые нанотрубки</kwd><kwd>2-карен</kwd><kwd>изобензофураны</kwd></kwd-group><kwd-group xml:lang="en"><kwd>3-carene</kwd><kwd>halloysite nanotubes</kwd><kwd>2-carene</kwd><kwd>isobenzofurans</kwd></kwd-group><funding-group><funding-statement xml:lang="ru">Исследование выполнено при финансовой поддержке БРФФИ (проект Х18МС-029).</funding-statement><funding-statement xml:lang="en">The research was performed with financial support of BRFFR (project Х18МС-029).</funding-statement></funding-group></article-meta></front><back><ref-list><title>References</title><ref id="cit1"><label>1</label><citation-alternatives><mixed-citation xml:lang="ru">Sheldon, R. A. Green and sustainable manufacture of chemicals from biomass: state of the art / R. A. Sheldon // Green Chem. - 2014. - Vol. 16, N 3. - 950-963. https://doi.org/10.1039/c3gc41935e</mixed-citation><mixed-citation xml:lang="en">Sheldon R. A. Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chemistry, 2014, vol. 16, no. 3, pp. 950-963. https://doi.org/10.1039/c3gc41935e</mixed-citation></citation-alternatives></ref><ref id="cit2"><label>2</label><citation-alternatives><mixed-citation xml:lang="ru">Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans / T. D. Bateman [et al.] // Bioorg. Med. Chem. Lett. - 2009. - Vol. 19, N 24. - P. 6898-6901. https://doi.org/10.1016/j.bmcl.2009.10.079</mixed-citation><mixed-citation xml:lang="en">Bateman T. D., Joshi A. L., Moon K., Galitovskaya E. N., Upreti M., Chambers T. C., McIntosh M. C. Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans. Bioorganic &amp; Medicinal Chemistry Letters, 2009, vol. 19, no. 24, pp. 6898-6901. https://doi.org/10.1016/j.bmcl.2009.10.079</mixed-citation></citation-alternatives></ref><ref id="cit3"><label>3</label><citation-alternatives><mixed-citation xml:lang="ru">Palladium-catalyzed heteroallylation of unactivated alkenes - synthesis of citalopram / J. F. M. Hewitt [et al.] // Chem. Sci. - 2013. - Vol. 4, N 9 - P. 3538-3543. https://doi.org/10.1039/c3sc51222c</mixed-citation><mixed-citation xml:lang="en">Hewitt J. F. M., Williams L., Aggarwal P., Smith C. D., France D. J. Palladium-catalyzed heteroallylation of unactivated alkenes - synthesis of citalopram. Chemical Science, 2013, vol. 4, no. 9, pp. 3538-3543. https://doi.org/10.1039/c3sc51222c</mixed-citation></citation-alternatives></ref><ref id="cit4"><label>4</label><citation-alternatives><mixed-citation xml:lang="ru">Antiplatelet activity of 3-butyl-6-bromo-1(3H)-isobenzofuranone on rat platelet aggregation / F. Ma [et al.] // J. Thromb. Thrombolysis. - 2012. - Vol. 33, N 1. - P. 64-73. https://doi.org/10.1007/s11239-011-0647-9</mixed-citation><mixed-citation xml:lang="en">Ma F., Gao Y., Qiao H., Hu X., Chang J. Antiplatelet activity of 3-butyl-6-bromo-1(3H)-isobenzofuranone on rat platelet aggregation. Journal of Thrombosis and Thrombolysis, 2012, vol. 33, no. 1, pp. 64-73. https://doi.org/10.1007/s11239-011-0647-9</mixed-citation></citation-alternatives></ref><ref id="cit5"><label>5</label><citation-alternatives><mixed-citation xml:lang="ru">Unusual reactions of (+)-Car-2-ene and (+)-Car-3-ene with aldehydes on K10 clay / I. V. Il'ina [et al.] // Helv. Chim. Acta. - 2010. - Vol. 93, N 11. - P. 2135-2150. https://doi.org/10.1002/hlca.201000145</mixed-citation><mixed-citation xml:lang="en">Il'ina I. V., Volcho K. P., Korchagina D. V., Salnikov G. E., Genaev A. M., Karpova E. V., Salakhutdinov N. F. Unusual reactions of (+)-Car-2-ene and (+)-Car-3-ene with aldehydes on K10 clay. Helvetica Chimica Acta, 2010, vol. 93, no. 11, pp. 2135-2150. https://doi.org/10.1002/hlca.201000145</mixed-citation></citation-alternatives></ref><ref id="cit6"><label>6</label><citation-alternatives><mixed-citation xml:lang="ru">Potent neuroprotective activity of monoterpene derived 4-[(3aR,7aS)-1,3,3a, 4,5,7a-hexahydro-3,3,6-trimethylisoben-zofuran-1-yl]-2-methoxyphenol in MPTP mice model / A. V. Pavlova [et al.] // Lett. Drug Design Discov. - 2014. - Vol. 11, N 5 - P. 611-617. https://doi.org/10.2174/1570180811666131210000316</mixed-citation><mixed-citation xml:lang="en">Pavlova A. V., Il'ina I. V., Morozova E. A., Korchagina D. V., Kurbakova S. Yu., Sorokina I. V., Tolstikova T. G., Volcho K. P., Salakhutdinov N. F. Potent neuroprotective activity of monoterpene derived 4-[(3aR,7aS)-1,3,3a,4,5,7a-hexahy-dro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol in MPTP mice model. Letters in Drug Design &amp; Discovery, 2014, vol. 11, no. 5, pp. 611-617. https://doi.org/10.2174/1570180811666131210000316</mixed-citation></citation-alternatives></ref><ref id="cit7"><label>7</label><citation-alternatives><mixed-citation xml:lang="ru">Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays / A. Yu. Sidorenko [et al.] // Mol. Catal. - 2018. - Vol. 459. - P. 38-45. https://doi.org/10.1016/j.mcat.2018.07.025</mixed-citation><mixed-citation xml:lang="en">Sidorenko A. Yu., Il'ina I. V., Kravtsova A. V., Aho A., Ardashov O. V., Li-Zhulanov N. S., Volcho K. P., Salakhutdinov N. F., Murzin D. Yu., Agabekov V. E. Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays. Molecular Catalysis, 2018, vol. 459, pp. 38-45. https://doi.org/10.1016/j.mcat.2018.07.025</mixed-citation></citation-alternatives></ref><ref id="cit8"><label>8</label><citation-alternatives><mixed-citation xml:lang="ru">Yuan, P. Properties and applications of halloysite nanotubes: recent research advances and future prospects / P. Yuan, D. Tan, F. Annabi-Bergaya // Appl. Clay Sci. - 2015. - Vol. 112-113. - P. 75-93. https://doi.org/10.1016/j.clay.2015.05.001</mixed-citation><mixed-citation xml:lang="en">Yuan P., Tan D., Annabi-Bergaya F. Properties and applications of halloysite nanotubes: recent research advances and future prospects. Applied Clay Science, 2015, vol. 112-113, pp. 75-93. https://doi.org/10.1016/j.clay.2015.05.001</mixed-citation></citation-alternatives></ref><ref id="cit9"><label>9</label><citation-alternatives><mixed-citation xml:lang="ru">Highly selective Prins reaction over acid-modified halloysite nanotubes for synthesis of isopulegol-derived 2H-chromene compounds / A. Yu. Sidorenko [et al.] // J. Catal. - 2019. - Vol. 374. - P. 360-377. https://doi.org/10.1016/j.jcat.2019.05.009</mixed-citation><mixed-citation xml:lang="en">Sidorenko A. Yu., Kravtsova A. V., Aho A., Heinmaa I., Warna J., Pazniak H., Volcho K. P., Salakhutdinov N. F., Murzin D. Yu., Agabekov V. E. Highly selective Prins reaction over acid-modified halloysite nanotubes for synthesis of isopulegol-derived 2H-chromene compounds. Journal of Catalysis, 2019, vol. 374, pp. 360-377. https://doi.org/10.1016/j.jcat.2019.05.009</mixed-citation></citation-alternatives></ref><ref id="cit10"><label>10</label><citation-alternatives><mixed-citation xml:lang="ru">Clay nanotubes catalyzed solvent-free synthesis of octahydro-2H-chromenols with pharmaceutical potential from (-)-isopulegol and ketones / A. Yu. Sidorenko [et al.] // J. Catal. - 2019. - Vol. 380. - P. 145-152. https://doi.org/10.1016/j.jcat.2019.10.015</mixed-citation><mixed-citation xml:lang="en">Sidorenko A. Yu., Kravtsova A. V., Il'ina I. V., Warna J., Korchagina D. V., Gatilov Yu. V., Volcho K. P., Salakhutdinov N. F., Murzin D. Yu., Agabekov V. E. Clay nanotubes catalyzed solvent-free synthesis of octahydro-2H-chromenols with pharmaceutical potential from (-)-isopulegol and ketones. Journal of Catalysis, 2019, vol. 380, pp. 145-152. https://doi.org/10.1016/j.jcat.2019.10.015</mixed-citation></citation-alternatives></ref><ref id="cit11"><label>11</label><citation-alternatives><mixed-citation xml:lang="ru">Catalytic isomerization of a-pinene and 3-carene in the presence of modified layered aluminosilicates / A. Yu. Sidorenko [et al.] // Mol. Catal. - 2017. - Vol. 443. - P. 193-202. https://doi.org/10.1016/j.mcat.2017.10.014</mixed-citation><mixed-citation xml:lang="en">Sidorenko A. Yu., Aho A., Ganbaatar J., Batsuren D., Utenkova D. B., Sen'kov G. M., Warna J., Murzin D. Yu., Agabekov V. E. Catalytic isomerization of a-pinene and 3-carene in the presence of modified layered aluminosilicates. Molecular Catalysis, 2017, vol. 443, pp. 193-202. https://doi.org/10.1016/j.mcat.2017.10.014</mixed-citation></citation-alternatives></ref><ref id="cit12"><label>12</label><citation-alternatives><mixed-citation xml:lang="ru">NMR and GC analyses of 3-carene isomerization products over activated glauconite / D. B. Utenkova [et al.] // J. Appl. Spect. - 2017. - Vol. 83, N 6. - P. 1026-1030. https://doi.org/10.1007/s10812-017-0401-y</mixed-citation><mixed-citation xml:lang="en">Utenkova D. B., Skakovskii E. D., Senkov G. M., Agabekov V. E., Baranovskii A. V., Bogushevich S. E., Sidorenko A. Yu. NMR and GC Analyses of 3-Carene Isomerization Products over Activated Glauconite. Journal of Applied Spectroscopy, 2017, vol. 83, no. 6, pp. 1026-1030. https://doi.org/10.1007/s10812-017-0401-y</mixed-citation></citation-alternatives></ref></ref-list><fn-group><fn fn-type="conflict"><p>The authors declare that there are no conflicts of interest present.</p></fn></fn-group></back></article>
