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<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="en"><front><journal-meta><journal-id journal-id-type="publisher-id">chemicallytech</journal-id><journal-title-group><journal-title xml:lang="en">Fine Chemical Technologies</journal-title><trans-title-group xml:lang="ru"><trans-title>Тонкие химические технологии</trans-title></trans-title-group></journal-title-group><issn pub-type="ppub">2410-6593</issn><issn pub-type="epub">2686-7575</issn><publisher><publisher-name>MIREA – Russian Technological University (RTU MIREA).</publisher-name></publisher></journal-meta><article-meta><article-id custom-type="elpub" pub-id-type="custom">chemicallytech-565</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="en"><subject>CHEMISTRY AND TECHNOLOGY OF MEDICINAL COMPOUNDS AND BIOLOGICALLY ACTIVE SUBSTANCES</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="ru"><subject>ХИМИЯ И ТЕХНОЛОГИЯ ЛЕКАРСТВЕННЫХ ПРЕПАРАТОВ И БИОЛОГИЧЕСКИ АКТИВНЫХ СОЕДИНЕНИЙ</subject></subj-group></article-categories><title-group><article-title>SYNTHESIS AND STUDY OF THE PHOTOCHROMIC BEHAVIOR OF SUBSTITUTED 6'-NITRO-1,3,3-TRIMETHYL-5-VINYLSPIRO(INDOLINO-2,2'-[2H]CHROMENES)</article-title><trans-title-group xml:lang="ru"><trans-title>ПОЛУЧЕНИЕ И ИЗУЧЕНИЕ ФОТОХРОМНОГО ПОВЕДЕНИЯ ЗАМЕЩЕННЫХ 5-ВИНИЛ-6'-НИТРО-1,3,3-ТРИМЕТИЛ-СПИРО(ИНДОЛИНО-2,2'-[2H]-ХРОМЕНОВ)</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>Лаптев</surname><given-names>А. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Laptev</surname><given-names>A. V.</given-names></name></name-alternatives><bio xml:lang="ru"><p>кафедра Биотехнологии и бионанотехнологии, научный сотрудник</p></bio><email xlink:type="simple">biolapa@inbox.ru</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>Лукин</surname><given-names>А. Ю.</given-names></name><name name-style="western" xml:lang="en"><surname>Lukin</surname><given-names>A. Yu.</given-names></name></name-alternatives><bio xml:lang="ru"><p>кафедра Биотехнологии и бионанотехнологии, доцент</p></bio><email xlink:type="simple">noemail@neicon.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>Беликов</surname><given-names>Н. Е.</given-names></name><name name-style="western" xml:lang="en"><surname>Belikov</surname><given-names>N. V.</given-names></name></name-alternatives><bio xml:lang="ru"><p>кафедра Биотехнологии и бионанотехнологии, научный сотрудник</p></bio><email xlink:type="simple">noemail@neicon.ru</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>Демина</surname><given-names>О. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Demina</surname><given-names>O. V.</given-names></name></name-alternatives><bio xml:lang="ru"><p>старший научный сотрудник</p></bio><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-3"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Варфоломеев</surname><given-names>С. Д.</given-names></name><name name-style="western" xml:lang="en"><surname>Varfolomeev</surname><given-names>S. D.</given-names></name></name-alternatives><bio xml:lang="ru"><p>директор</p></bio><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-3"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Барачевский</surname><given-names>В. А.</given-names></name><name name-style="western" xml:lang="en"><surname>Barachevsky</surname><given-names>V. A.</given-names></name></name-alternatives><bio xml:lang="ru"><p>заведующий лабораторией</p></bio><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-4"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Ходонов</surname><given-names>А. А.</given-names></name><name name-style="western" xml:lang="en"><surname>Khodonov</surname><given-names>A. A.</given-names></name></name-alternatives><bio xml:lang="ru"><p>кафедра Биотехнологии и бионанотехнологии, профессор</p></bio><email xlink:type="simple">noemail@neicon.ru</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>Швец</surname><given-names>В. И.</given-names></name><name name-style="western" xml:lang="en"><surname>Shvets</surname><given-names>V. I.</given-names></name></name-alternatives><bio xml:lang="ru"><p>кафедра Биотехнологии и бионанотехнологии, заведующий кафедрой</p></bio><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-5"/></contrib></contrib-group><aff-alternatives id="aff-1"><aff xml:lang="ru"><institution>МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86; &#13;
Институт биохимической физики им. Н.М. Эмануэля РАН, Москва, 119334</institution><country>Россия</country></aff><aff xml:lang="en"><institution>M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571; &#13;
N.M. Emanuel Institute of Biochemical Physics RAS, Moscow, 119334</institution><country>Russian Federation</country></aff></aff-alternatives><aff-alternatives id="aff-2"><aff xml:lang="ru"><institution>МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86;</institution><country>Россия</country></aff><aff xml:lang="en"><institution>M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571</institution><country>Russian Federation</country></aff></aff-alternatives><aff-alternatives id="aff-3"><aff xml:lang="ru"><institution>Институт биохимической физики им. Н.М. Эмануэля РАН, Москва, 119334</institution><country>Россия</country></aff><aff xml:lang="en"><institution>N.M. Emanuel Institute of Biochemical Physics RAS, Moscow, 119334</institution><country>Russian Federation</country></aff></aff-alternatives><aff-alternatives id="aff-4"><aff xml:lang="ru"><institution>Центр фотохимии РАН, Москва, 119421</institution><country>Россия</country></aff><aff xml:lang="en"><institution>Photochemistry Center RAS, Moscow, 119421</institution><country>Russian Federation</country></aff></aff-alternatives><aff-alternatives id="aff-5"><aff xml:lang="ru"><institution>МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86</institution><country>Россия</country></aff><aff xml:lang="en"><institution>M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571</institution><country>Russian Federation</country></aff></aff-alternatives><pub-date pub-type="collection"><year>2013</year></pub-date><pub-date pub-type="epub"><day>28</day><month>08</month><year>2013</year></pub-date><volume>8</volume><issue>4</issue><fpage>18</fpage><lpage>26</lpage><permissions><copyright-statement>Copyright &amp;#x00A9; Laptev A.V., Lukin A.Y., Belikov N.V., Demina O.V., Varfolomeev S.D., Barachevsky V.A., Khodonov A.A., Shvets V.I., 2013</copyright-statement><copyright-year>2013</copyright-year><copyright-holder xml:lang="ru">Лаптев А.В., Лукин А.Ю., Беликов Н.Е., Демина О.В., Варфоломеев С.Д., Барачевский В.А., Ходонов А.А., Швец В.И.</copyright-holder><copyright-holder xml:lang="en">Laptev A.V., Lukin A.Y., Belikov N.V., Demina O.V., Varfolomeev S.D., Barachevsky V.A., Khodonov A.A., Shvets V.I.</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://www.finechem-mirea.ru/jour/article/view/565">https://www.finechem-mirea.ru/jour/article/view/565</self-uri><abstract><p>Few 5-vinyl substituted 6’-nitro-1,3,3-trimethylspiro(indolino-2,2’-[2H]chromenes) (6’-nitro-spiropyrans) were synthesized by a one-step method from 5-formyl precursor – 5-formyl-6’-nitro-1,3,3-trimethylspiro(indolino-2,2’- [2H]chromene) (1). 5-Vinyl-6’-nitro-spiropyran (2) was prepared by the Wittig olefination of 1 with an ylide, which was generated by the action of potassium tert-butylate on methyltriphenylphosphonium bromide in THF. E-6’- Nitro-5-(1’’-nitroethene-2’’-yl)-6’-nitro-spiropyran (3) was obtained by heating 1, nitromethane, ethylenediammonium diacetate at 50°С in absolute methanol and inert atmosphere. Compounds 1’’-[6’-nitro-spiropyran-5- yl]-2’’,2’’-dicyanoethylene (4) and E-1’’-[6’-nitro-spiropyran-5-yl]-2’’-cyano-2’’-methoxycarbonylethylene (5) were prepared from initial 1 by reflux in ammonium acetate / glacial acetic acid / benzene mixture with malonodinitrile or methyl 2-cyanoacetate, respectively. The procedure for synthesizing derivatives 2’’,2’’-dimethyl-5’’-(6’-nitrospiropyran-5-yl)methylidene-1’’,3’’-dioxane-4’’,6’’-dion (6) and 5’’,5’’-dimethyl-2’’-(6’-nitro-spiropyran-5-yl)- methylidenecyclohexane-1’’,3’’-dion (7) includes the interaction of Meldrum's acid or dimedone, accordingly, with 5-formyl precursor 1 by heating in ethanol in the presence of piperidine and molecular sieves (to bind the released water). The structures of the prepared compounds and their purity have been confirmed by physico-chemical analysis. A spectral kinetic study of the photochromic properties of the substituted 5-vinyl spiropyrans was carried out in toluene and ethanol solutions. The 5-vinyl-6’-nitro-spiropyran derivatives 2–7 described in this work are of interest for further synthetic transformations.</p></abstract><trans-abstract xml:lang="ru"><p>Ряд замещенных 5-винил-6’-нитро-1,3,3-триметилспиро(индолино-2,2’-[2H]-хроменов) был получен одностадийными методами синтеза из 5-формильного предшественника. Структуры полученных соединений подтверждены методами физико-химического анализа. Проведены спектрально-кинетические исследования фотохромного поведения новых 5-винилзамещенных продуктов в растворах толуола и этанола.</p></trans-abstract><kwd-group xml:lang="ru"><kwd>спиропиран</kwd><kwd>фотохромизм</kwd><kwd>винилог</kwd><kwd>CH-кислота</kwd><kwd>реакция олефинирования</kwd><kwd>фотохромная метка</kwd></kwd-group><kwd-group xml:lang="en"><kwd>spiropyrans</kwd><kwd>photochromism</kwd><kwd>vinilogs</kwd><kwd>CH-acid</kwd><kwd>olefination reaction</kwd><kwd>photochromic label.</kwd></kwd-group></article-meta></front><back><ref-list><title>References</title><ref id="cit1"><label>1</label><citation-alternatives><mixed-citation xml:lang="ru">Photochromism: Techniques in Chemistry / Ed. G.Y. Brown. -New York: Wiley Interscience, 1971. V. III. 853 p.</mixed-citation><mixed-citation xml:lang="en">Photochromism: Techniques in Chemistry / Ed. G.Y. Brown. -New York: Wiley Interscience, 1971. V. 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