СИНТЕЗ N-ГИДРОКСИИНДОЛОВ

  • Zhanna V. Chirkova Ярославский государственный технический университет
Ключевые слова: N-гидроксииндолы, внутримолекулярная восстановительная циклизация, [3 2]-циклоприсоединение, дезоксигенирование, каталитическое окисление, орто-замещенные нитро- и нитрозоароматические соединения, 2, 3-дигидроиндолы

Аннотация

В данном обзоре рассмотрены основные синтетические подходы для получения N-гидроксииндолов. Первый подход заключается во внутримолекулярной восстановительной циклизации орто-замещенных нитроароматических соединений различными химическими восстановителями. В качестве субстратов для синтеза N-гидроксииндолов используются 2-нитрофенилацетальдегиды (синтез по Ачесону), N,N-дизамещенные амино-2-нитростиролы (синтез по Сомею), орто-нитрокетоэфиры различного строения или 1-(o-нитроарил)-1-цианоалкены, орто-нитрокетоны, орто-нитрофенилацетонитрилы. В качестве восстановителей применяются треххлористый титан, цинк либо в присутствии хлористого аммония, либо в уксусной кислоте, двухлористое олово, а также водород с использованием катализаторов на основе благородных металлов (платина, палладий). Вторым подходом является [3+2]-циклоприсоединение нитрозоароматических соединений к алкинам или дезоксигенирование орто-замещенных нитроароматических соединений с последующей внутримолекулярной циклизацией. Третий подход представляет собой каталитическое окисление 2,3-дигидроиндолов или индолов различного строения концентрированной перекисью водорода в присутствии каталитических количеств вольфрамата натрия. Особое внимание уделено синтезу функциональных производных N-гидроксииндол-5,6-дикарбоновых кислот. Это обусловлено тем, что данные соединения, как правило, синтезируют из коммерчески доступного сырья без использования дорогостоящих катализаторов, применяя хорошо известные и отработанные методы синтеза. При этом удалось получать индолы различного дизайна, которые, например, могут являться основными билдинг-блоками для синтеза БАВ, фталоцианинов различного строения, обладающих жидкокристаллическими и каталитическими свойствами. Представители этого класса гетероциклов встречаются среди многочисленных природных соединений, могут быть использованы в качестве терапевтических агентов, например, как ингибиторы человеческой лактатдегидрогеназы изоформы 5, селективные ингибиторы моноаминооксидазы А и Б, а N-метоксииндолы могут применяться для лечения рака молочной железы.

Для цитирования:

Чиркова Ж.В. Синтез N-гидроксииндолов. Изв. вузов. Химия и хим. технология. 2017. Т. 60. Вып. 4. С. 4-20.



Литература

Radwanski E.R., Last R.L. Tryptophan Biosynthesis and Metabolism: Biochemical and Molecular Genetics. The Plant Cell. 1995. V. 7. P. 921-934. DOI: 10.1105_tpc.7.7.921.

Somei M., Fukui Y., Hasegawa M., Oshikiri N., Hayashi T. Syntheses of melatonin and the derivatives. Heterocycles. 2000. V. 53. N 8. P. 1725-1736. DOI: 10.3987/COM-00-8930.

Reyes F., Fernandez R., Rodriguez A., Francesch A., Taboada S., Avila C., Cuevas C. Aplicyanins A–F, new cytotoxic bromoindole derivatives from the marine tunicate Aplidium cyaneum. Tetrahedron. 2008. V. 64. N 22. P. 5119-5123. DOI: 10.1016/j.tet.2008.03.060.

Bartsch A., Bross M., Spiteller P., Spiteller M., Steglich W. Birnbaumin A and B: Two Unusual 1-Hydroxyindole Pigments from the “Flower Pot Parasol” Leucocoprinus birnbaumii. Angew. Chem. Int. Ed. 2005. V. 44. P. 2957-2959. DOI: 10.1002/anie.200500082.

Nicolaou K.C., Estrada A.A., Freestone G.C., Lee S.H., Alvarez-Mico X. New synthetic technology for the construction of N-hydroxyindoles and synthesis of nocathiacin I model systems. Tetrahedron. 2007. V. 63. N 27. P. 6088-6114. DOI: 10.1016/j.tet.2007.03.072.

Selvakumar N., Rajulu G.G. Efficient Total Syntheses of Phytoalexin and (±)-Paniculidine B and C Based on the Novel Meth-odology for the Preparation of 1-Methoxyindoles. J. Org. Chem. 2004. V. 69. N 13. P. 4429-4432. DOI: 10.1021/jo040134l.

Herzon S.B., Myers A.G. Enantioselective Synthesis of Stephacidin B. J. Am. Chem. Soc. 2005. V. 127. N 15. P. 5342–5344. DOI: 10.1021/ja0510616.

Granchi C., Roy S., Del Fiandra C., Tuccinardi T., Lanza M., Betti L., Giannaccini G., Lucacchini A., Martinelli A., Mac-chia M., Minutolo F. Triazole-substituted N-hydroxyindol-2-carboxylates as inhibitors of isoform 5 of human lactate dehydro-genase (hLDH5). Med. Chem. Commun. 2011. V. 2. P. 638-643. DOI: 10.1039/c1md00071c.

Granchi C., Roy S., Giacomelli C., Macchia M., Tuccinardi T., Martinelli A., Lanza M., Betti L., Giannaccini G., Lucac-chini A., Funel N., Leon L.G., Giovannetti E., Peters G.J., Palchaudhuri R., Calvaresi E.C., Hergenrother P.J., Minutolo F. Discovery of N-Hydroxyindole-Based Inhibitors of Human Lactate Dehydrogenase Isoform A (LDH-A) as Starvation Agents against Cancer Cells. J. Med. Chem. 2011. V. 54. P. 1599-1612. DOI: 10.1021/jm101007q.

Granchi C., Roy S., Mottinelli M., Nardini E., Campinoti F., Tuccinardi T., Lanza M., Betti L., Giannaccini G., Lucacchi-ni A., Martinelli A., Macchia M., Minutolo F. Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibi-tors of human lactate dehydrogenase-isoform 5. Bioorg. Med. Chem. Lett. 2011. V. 21. P. 7331-7336. DOI: 10.1016/j.bmcl.2011.10.031.

Granchi C., Roy S., De Simone A., Salvetti I., Tuccinardi T., Martinelli A., Macchia M., Lanza M., Betti L., Giannaccini G., Lucacchini A., Giovannetti E., Sciarrillo R., Peters G.J., Minutolo F. N-Hydroxyindole-based inhibitors of lactate dehy-drogenase against cancer cell proliferation. Eur. J. Med. Chem. 2011. V. 46. P. 5398-5407. DOI: 10.1016/j.ejmech.2011.08.046.

Chirkova Zh.V., Kabanova M.V., Filimonov S.I., Abramov I.G., Petzer A., Petzer J.P., Firgang S.I., Suponitsky K.Yu. Inhibition of monoamine oxidase by indole-5,6-dicarbonitrile derivatives. Bioorg. Med. Chem. Lett. 2015. V. 25. P. 1206-1211. DOI: 10.1016/j.bmcl.2015.01.061.

Chirkova Zh.V., Kabanova M.V., Filimonov S.I., Abramov I.G., Petzer A., Petzer J.P., Suponitsky K.Yu. An evaluation of synthetic indole derivatives as inhibitors of monoamine oxidase. Bioorg. Med. Chem. Lett. 2016. V. 26. P. 2214-2219. DOI: 10.1016/j.bmcl.2016.03.060.

Jump S.M., Kung J., Staub R., Kinseth M.A., Crama E.J., Yudina L.N., Preobrazhenskaya M.N., Bjeldanes L.F., Fire-stone G.L. N-Alkoxy derivatization of indole-3-carbinol increases the efficacy of the G1 cell cycle arrest and of I3C-specific regu-lation of cell cycle gene transcription and activity in human breast cancer cells. Biochem. Pharmacol. 2008. V. 75. P. 713–724. DOI: 10.1016/j.bcp.2007.09.024.

Shen Shu-Su, Kartika V., Tan Y.Sh., Webster R.D., Narasaka K. Selective aerobic oxidation of allylic and benzylic alcohols catalyzed by N-hydroxyindole and copper(I) chloride. Tetrahedron Lett. 2012. V. 53. P. 986–990. DOI: 10.1016/j.tetlet.2011.12.058.

Hong Y., Iqbal Z., Yin X., Cao D. Synthesis of double D-A branched organic dyes employing indole and phenoxazine as do-nors for efficient DSSCs. Tetrahedron. 2014. V. 70. P. 6296-6302. DOI: 10.1016/j.tet.2014.03.086.

Acheson R.M., Littlewood D.M., Rosenberg H.E. Synthesis of 1-methoxyindoles. J. Chem. Soc., Chem. Commun. 1974. V. 16. P. 671а-671а. DOI: 10.1039/C3974000671A.

Acheson R.M., Hunt P.G., Littlewood D.M., Murrer B.A., Rosenberg H.E. The Synthesis, Reactions, and Spectra of 1-Acetoxy-, 1-Hydroxy-, and 1-Methoxyindoles. J. Chem. Soc., Perkin I. 1978. P. 1117-1125. DOI: 10.1039/P19780001117.

Somei M. 1-Hydroxyindoles. Heterocycles. 1999. V. 50. N 2. P. 1157-1211. DOI: 10.3987/REV-98-SR(H)8.

Somei M., Shoda T. A facile route to 1-Acetoxy- and 1-Me-thoxyindoles. Heterocycles. 1981. V. 16. N 9. P. 1523-1525. DOI: 10.3987/R-1981-09-1523.

Somei M., Inoue S., Tokutake S., Yamada F., Kaneko C. The Chemistry of Indoles. XIII. Syntheses of Substituted Indoles carrying: Amino, Nitro, Methoxycarbonyl, or Benzoloxy Group at the 4-Position and Their 1-Hydroxy Derivatives. Chem. Pharm. Bull. 1981. V. 29. N 3. P. 726-738. DOI: 10.1248/cpb.29.726.

Somei M., Tsuchiya M. The Chemistry of Indoles. XVI. A Convenient Synthesis of Substituted Indoles carrying a Hydroy Group, a Halageno Group, or a Carbon Side Chain at the 4-Position via 4-Indolediazonium Saits and a Total Synthesis of (±)-6,7-Secoagroclavine. Chem. Pharm. Bull. 1981. V. 29. N 11. P. 3145-3157. DOI: 10.1248/cpb.29.3145.

Somei M., Sato H., Komura N., Kaneko C. Synthetic study for 1-Methoxyindoles and 1-Methoxy-2-oxindoles. Heterocycles. 1985. V. 23. N 5. P. 1101 - 1106. DOI: 10.3987/R-1985-05-1101.

Somei M., Ohnishi H. Total synthesis of (±)-Paniculidine B. Chem. Pharm. Bull. 1985. V. 33. N 11. P. 5147 – 5148. DOI: 10.1248/cpb.33.5147.

Somei M., Ohnishi H., Shoken Y. The Chemistry of Indoles. XXVII. A Practical Synthesis of the1-Methoxy Analog of an Ergot Alkaloid, (+)-l-Methoxy-6,7-secoagroclavine. Chem. Pharm. Bull. 1986. V. 34. N 2. P. 677 – 681. DOI: 10.1248/cpb.34.677.

Somei M. The Chemistry of Indoles. XXXII. A Facile Synthetic Method for 6-Indolecarbaldehyde, 6-Indolemethanol, and 6-Substituted I-Hydroxyindoles and Its Application for the Synthesis of a Natural Alkaloid, (E)-6-(3-Methylbuta1,3-dienyl)indole. Chem. Pharm. Bull. 1986. V. 34. N 10. P. 4109 – 4115. DOI: 10.1248/cpb.34.4109.

Somei M., Saida Y., Komura N. The Chemistry of Indoles. XXXIII. Substituent Effect in Regioselective Metalation of 3-Indolecarbaldehyde and Syntheses of Indoles Carrying a Carbon Side Chain at the 4-, 5-, 6-, or 7-Position. Chem. Pharm. Bull. 1986. V. 34. N 10. P. 4116–4125. DOI: 10.1248/cpb.34.4116.

Vo Q.V., Trenerry C., Rochfort S., Wadeson J., Leyton C., Hughes A.B. Synthesis and anti-inflammatory activity of indole glucosinolates. Bioorg. Med. Chem. 2014. V. 22. P. 856–864. DOI: 10.1016/j.bmc.2013.12.003.

Sharunov V.S., Chirkova Zh.V., Filimonov S.I., Abramov I.G., Plakhtinskiy V.V. Synthesis of 1-hydroxy-1H-indole-5,6-dicarbonitriles based on 4-methyl-5-nitrophthalonitrile. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2012. V. 55. N 8. P. 8-12 (in Russian).

Abramov I.G., Lyskov V.B., Sharunov V.S., Shetnev А.А., Filimonov S.I., Plakhtinskiy V.V., Krasovskaya G.G. Synthe-sis of 4-alkylnitrophthalonitriles. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2008. V. 51. N 8. P. 18-20 (in Russian).

Leimgruber W., Batcho A.D. Third International Congress of Heterocyclic Chemisrty. Sendai, Japan, Aug. 1971. P. 462. (Ab-stracts of papers).

Batcho A.D., Leimgruber W. Patent US 3976639. 1976.

Clark R.D., Repke D.B. The Leimgruber-Batcho indole synthesis. Heterocycles. 1984. V. 22. N 1. P. 195-221. DOI: 10.3987/R-1984-01-0195.

Clark R.D., Repke D.B. Some observations on the formation of 1-hydroxyindoles in the leimgruber-batcho indole synthesis. J. Heterocyclic Chem. 1985. V. 22. N 1. P. 121-125. DOI: 10.1002/jhet.5570220130.

Nicolaou K.C., Estrada A.A., Freestone G.C., Lee S.H., Alvarez-Mico X. New synthetic technology for the construction of N-hydroxyindoles and synthesis of nocathiacin I model systems. Tetrahedron. 2007. V. 63. N 27. P. 6088-6114. DOI: 10.1016/j.tet.2007.03.072.

Nicolaou K.C., Lee S.H., Estrada A.A., Zak M. Construction of Substituted N-Hydroxyindoles: Synthesis of a Nocathiacin I Model System. Angew. Chem. Int. Ed. 2005. V. 44. N 24. P. 3736 – 3740. DOI: 10.1002/anie.200500724.

Nicolaou K.C., Estrada A.A., Lee S.H., Freestone G.C. Synthesis of Highly Substituted N-Hydroxyindoles through 1,5-Addition of Carbon Nucleophiles to In Situ Generated Unsaturated Nitrones. Angew. Chem. Int. Ed. 2006. V. 45. N 32. P. 5364 –5368. DOI: 10.1002/anie.200601808.

Minutolo F., Macchia M., Granchi C., Di Bussolo V., Giannaccini G., Lucacchini A., Hergenrother P.J., Calvaresi E.C. Patent US 20140343001. 2014.

Park Y.K., Kim H., Lee S.H. Synthesis of New Highly Substituted and Hindered 1-Hydroxyindole-2-carboxylates. Bull. Korean Chem. Soc. 2016. V. 37. P. 82–90. DOI: 10.1002/bkcs.10630.

Park Y.K., Kim H., Kim D.S., Cho H., Moon A., Jeong Ch., Yoon H.-R., Lee S.H. Synthesis of New 2,3-Disubstituted 4-Chloro-1-hydroxyindoles. Bull. Korean Chem. Soc. 2015. V. 36. P. 2095–2100. DOI: 10.1002/bkcs.10410.

Li B., Williams J.D., Peet N.P. Two concise total syntheses of the wasabi phytoalexin methyl 1-methoxyindole-3-carboxylate. Tetrahedron Lett. 2013. V. 54. N 24. P. 3124–3126. DOI: 10.1016/j.tetlet.2013.04.009.

Taber D.F., Tirunahari P.K. Indole synthesis: a review and proposed classification. Tetrahedron. 2011. V. 67. P. 7195-7210. DOI: 10.1016/j.tet.2011.06.040.

Wrobel Z., Makosza M. Transformations of o-Nitroarylallyl Carbanions. Synthesis of Quinoline N-Oxides and N-Hydroxyindoles. Tetrahedron. 1993. V. 49. N 24. P. 5315-5326. DOI: 10.1016/S0040-4020(01)82380-2.

Camara H.D., Attar K., Benchidmi M., Essassi E.M., Garri-ques B. Synthesis of new 1-hydroxyindole derivatives. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004. V. 43. P. 660-666.

Bujok R., Wróbel Z., Wojciechowski K. Expedient Synthesis of 1-Hydroxy-4- and 1-Hydroxy-6-nitroindoles. Synlett. 2012. V. 23. P. 1315–1320. DOI: 10.1055/s-0031-1291044.

Myers A.G., Herzon S.B. Identification of a Novel Michael Acceptor Group for the Reversible Addition of Oxygen- and Sulfur-Based Nucleophiles. Synthesis and Reactivity of the 3-Alkylidene-3H-indole 1-Oxide Function of Avrainvillamide. J. Am. Chem. Soc. 2003. V. 125. N 40. P. 12080-12081. DOI: 10.1021/ja0372006.

Minutolo F., Macchia M., Granchi C., Di Bussolo V., Giannaccini G., Lucacchini A., Hergenrother P.J. Patent WO2013/92753. 2013.

Wong A., Kuethe J.T., Davies Ia.W. A General Synthesis of N-Hydroxyindoles. J. Org. Chem. 2003. V. 68. P. 9865-9866. DOI: 10.1021/jo035351l.

Preston P.N., Tennant G. Synthetic methods involving neighboring group interaction in ortho-substituted nitrobenzene deriva-tives. Chem. Rev. 1972. V. 72. N 6. P. 627-677. DOI: 10.1021/cr60280a002.

Wong A., Kuethe J.T., Davies Ia.W., Hughes D.L. Synthesis of Novel KDR Kinase Inhibitors through Catalytic Reductive Cyclization of o-Nitrobenzylcarbonyl Compounds. J. Org. Chem. 2004. V. 69. P. 7761-7764. DOI: 10.1021/jo048843m.

Attar K., Camara H.D., Benchidmi M., Essassi Ε.M., Pierrot M. Synthesis of new 1-hydroxyindoles functionalized on posi-tion 3 by cyclizing reduction. Heterocycl. Comm. 2003. V. 9. N 4. P. 373–376. DOI: 10.1515/HC.2003.9.4.373.

Filimonov S.I., Chirkova Zh.V., Abramov I.G., Firgang S.I., Stashina G.A., Strelenko Yu.A., Khakimov D.V., Pivina T.S., Samet A.V., Suponitsky K.Yu. Base-induced transformations of ortho-nitrobenzylketones: intramolecular displacement of nitro group versus nitro-nitrite rearrangement. Tetrahedron. 2012. V. 30. P. 5991-5997. DOI: 10.1016/j.tet.2012.05.034.

Ivanovskii S.А., Dorogov М.V., Abramov I.G., Smirnov А.V. RF Patent № 2167855. 2002. (in Russian)

Maurin C., Bailly F., Cotelle Ph. Improved preparation and structural investigation of 4-aryl-4-oxo-2-hydroxy-2-butenoic acids and methyl esters. Tetrahedron. 2004. V.60. P. 6479-6486. DOI: 10.1016/j.tet.2004.06.030.

Chirkova Zh.V., Kabanova M.V., Sergeev S.S., Filimonov S.I., Abramov I.G., Samet A.V., Suponitsky K.Yu. Synthesis of 3-acyl-1-hydroxy-1H-indole-5,6-dicarbonitriles. Mendeleev Comm. 2015. V. 25. N 4. P. 315-317. DOI: 10.1016/j.mencom.2015.07.030.

Chirkova Zh.V., Kabanova M.V., Filimonov S.I. Synthesis of functional derivatives of 3-acyl-1-hydroxyindole5,6-dicarboxylic acid. Ros. Khim. Zhurnal (Zhurnal Ros. Khim. Obcsh. im. D. I. Mendeleeva). 2016. V. LX. N 5. P. 94-98. (in Russian).

Belley M., Sauer E., Beaudoin D., Duspara P., Trimble L.A., Dube P. Synthesis and reactivity of N-hydroxy-2-aminoindoles. Tetrahedron Lett. 2006. V. 47. N 2. P. 159 - 162. DOI: 10.1016/j.tetlet.2005.10.165

Forbec T., Helen K., Morgan A. A Synthesis of novel 1H-Imidazo[1,2-α]Indole-3-Carboxylates. Synth. Comm. 1996. V. 26. N 4. P. 745-754. DOI: 10.1080/00397919608086749

Showalter H., Bridgec A.J., Zhou H. Tyrosine kinase inhibitors. 16. 6,5,6-tricyclic benzothieno[3,2-d]pyrimidines and pyrim-ido[5,4-b-] and [4,5-b]ĭndoles as potent inhibitors of the epidermal growth factor receptor tyrosine kinase. J. Med. Chem. 1999. V. 42. N 26. P. 5464-5474. DOI: 10.1021/jm9903949.

Santen Pharmaceutical Co. Ltd; Patent EP2119703. 2009.

Stephensen H., Zaragoza F. Solid-Phase Synthesis of N-Hydroxyindoles and Benzo[c]isoxazoles by C-Arylation of Substituted Acetonitriles and 1,3-Dicarbonyl Compounds with Polystyrene-bound Aryl Fluorides. Tetrahedron Lett. 1999. V. 40. N 31. P. 5799-5802. DOI: 10.1016/S0040-4039(99)01117-X.

Belley M., Beaudoin D., Duspara P., Sauer E., St-Pierre G., Trimble L.A. Synthes is and React ivity of N-Hydroxy-2-Amino-3-Arylindoles. Synlett. 2007. V. 19. P. 2991-2994. DOI: 10.1055/s-2007-990969.

Kawasaki T., Tabata M., Nakagawa K., Kobayashi K., Kodama A., Kobayashi T., Hasegawa M., Tanii K., Somei M. Simple Synthetic Method for 1-Hydroxyindole and Its Application to 1-Hydroxytryptophan Derivatives. Heterocycl. 2015. V. 90. N 2. P. 1038-1071. DOI: 10.3987/COM-14-S(K)74.

Wrobel Z., Makosza M. Synthesis of l-Hydroxyindoles and lndoles from ortho-Nitroarylethanes. Tetrahedron. 1997. V. 53. N 15. P. 5501-5514. DOI: 10.1016/S0040-4020(97)00208-1.

Filimonov S.I., Chirkova Zh.V., Sharunov V.S., Abramov I.G., Stashina G.A., Firgang S.I., Suponitsky K.Yu. Synthesis of 3-substituted 2-amino-1-hydroxy-1H-indole-5,6-dicarbonitriles. Chem. Heterocycl. Compd. 2012. V. 48. N 3. P. 427-435. DOI: 0009-3122/12/4803-0427.

Ieronimo G., Mondelli A., Tibiletti F., Maspero A., Palmisano G., Galli S., Tollari S., Masciocchi N., Nicholas K.M., Tagli-apietra S., Cravotto G., Penoni A. A simple, efficient, regioselective and one-pot preparation of N-hydroxy- and N-O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic scope, applications and novel by-products. Tetrahedron. 2013. V. 69. P. 10906-10920. DOI: 10.1016/j.tet.2013.10.072.

Penoni A., Palmisano G., Broggini G., Kadowaki Ay., Nicholas K.M. Efficient Synthesis of N-Methoxyindoles via Alkylative Cycloaddition of Nitrosoarenes with Alkynes. J. Org. Chem. 2006. V. 71. P. 823-825. DOI: 10.1021/jo051609r.

Penoni A., Palmisano G., Zhao Yi-Lei, Houk K.N., Volkman J., Nicholas K.M. On the Mechanism of Nitrosoarene-Alkyne Cycloaddition. J. Am. Chem. Soc. 2009. V. 131. P. 653–661. DOI: 10.1021/ja806715u.

Penoni A., Volkmann J., Nicholas K.M. Regioselective Synthesis of Indoles via Reductive Annulation of Nitrosoaromatics with Alkynes. Org. Lett. 2002. V. 4. N 5. P. 699-701. DOI: 10.1021/ol017139e.

Tibiletti F., Simonetti M., Nicholas K.M., Palmisano G., Parravicini M., Imbesi F., Tollari S., Penoni A. One-pot synthesis of meridianins and meridianin analogues via indolization of nitrosoarenes. Tetrahedron. 2010. V. 66. P. 1280–1288. DOI: 10.1016/j.tet.2009.12.020.

Penoni A., Nicholas K.M. A novel and direct synthesis of indoles via catalytic reductive annulation of nitroaromatics with al-kynes. Chem. Commun. 2002. N 5. P. 484-485. DOI: 10.1039/b110370a.

Ragaini F., Rapetti A., Visentin E., Monzani M., Caselli A., Cenini S. Synthesis of Indoles by Intermolecular Cyclization of Unfunctionalized Nitroarenes and Alkynes, Catalyzed by Palladium Phenanthroline Complexes. J. Org. Chem. 2006.

V. 71. N 10. P. 3748-3753. DOI: 10.1021/jo060073m.

Ragaini F., Ventriglia F., Hagar M., Fantauzzi S., Cenini S. Synthesis of Indoles by Intermolecular Cyclization of Unfunction-alized Nitroarenes and Alkynes: One-Step Synthesis of the Skeleton of Fluvastatin. Eur. J. Org. Chem. 2009. N 13. P. 2185-2189. DOI: 10.1002/ejoc.200801274.

Sundberg R.J. Deoxygenation of Nitro Groups by Trivalent Phosphorus. Indoles from o-Nitrostyrenes. J. Org. Chem. 1965. V. 30. N 11. P. 3604-3610. DOI: 10.1021/jo01022a006.

Bunyan P.J., Cadogan J.I.G. The Reactivity of Organophosphorus Compounds. Part XIV.1 Deoxygenation of Aromatic C-Nitrosocompounds by Triethyl Phosphite and Triphenylphosphine: a New Cyclisation Reaction. J. Chem. Soc. 1963. P. 42-49. DOI: 10.1039/JR9630000042.

Russell G.A., Yao Ching-Fa, Tashtoush H.I., Russell J.E., Dedolph D.F. Addition, Substitution, and Deoxygenation Reac-tions of a-Phenyl-p-nitrostyrenes with the Anions of Thiols and Diethyl Phosphite: Formation of Indoles by Reaction with Ethyl Phosphites. J. Org. Chem. 1991. V. 56. P. 663-669. DOI: 10.1021/jo00002a032.

Person H., Del Aguila Pardo M., Foucaud A. Reaction des isonitriles avec les β-nitrostyrenes, β-substitues. Nouvelle synthese ms hydroxy-1-indoles. Tetrahedron Lett. 1980. V. 21. P. 281-284. DOI: 10.1016/S0040-4039(00)71189-0.

Majgier-Baranowska H., Williams J.D., Li B., Peet N.P. Studies on the mechanism of the Cadogan–Sundberg indole synthesis. Tetrahedron Lett. 2012. V. 53. P. 4785-4788. DOI: 10.1016/j.tetlet.2012.06.146.

Davies Ia.W., Guner V.A., Houk K.N. Theoretical Evidence for Oxygenated Intermediates in the Reductive Cyclization of Ni-trobenzenes. Org. Lett. 2004. V. 6. N 5. P. 743-746. DOI: 10.1021/ol0364273.

Somei M., Kawasaki T. A new and simple synthesis of 1-hydroxyindole derivatives. Heterocycles. 1989. V. 29. N 7. P. 1251-1254. DOI: 10.3987/COM-89-5037.

Somei M., Kawasaki T., Shimizu K., Fukui Y., Ohta T. The Chemistry of 1-hydroxyindoles: Syntheses of methyl 1-hydroxyindole-3-acetate, Nb-acetyl-1-hydroxytryptamine, (±)- and (S)-1-hydroxytryptophan derivatives. Chem. Pharm. Bull. 1991. V. 39. N 7. P. 1905–1907. DOI: 10.1248/cpb.39.1905.

Kawasaki T., Kodama A., Nishida T., Shimizu K., Somei M. Preparation of 1-hydroxyindole derivatives and a new route to 2-substituted indoles. Heterocycles. 1991. V. 32. N 2. P. 221-227. DOI: 10.3987/COM-90-5647.

Somei M., Yamada F., Morikawa H. Syntheses of Serotonin, N-Methylserotonin, Bufotenine, and Melatonin, and the First Total Synthesis of N-(Indol-3-yl)methyl-N-methyl-5-methoxytryptamine from Tryptamine through a Common Intermediate, 1-Hydroxytryptamine. Heterocycles. 1997. V. 46. N 1. P. 91-94. DOI: 10.3987/COM-97-S33.

Somei M., Kobayashi K. A Regioselective Lithiation of 1-Methoxymethoxyindole at the 2-Position and Its Application for the Synthesis of 2-Substituted Indoles. Heterocycles. 1992. V. 34. N 7. P. 1295-1298. DOI: 10.3987/COM-92-6066.

Somei M., Kobayashi K., Tanii K., Mochizuki T., Kawada Y., Fukui Y. Simple Syntheses of Lespedamine and 5-Bromo-N,N-dimethyltryptamine Based on 1-Hydroxyindole Chemistry. Heterocycles. 1995. V. 40. N 1. P. 119-122. DOI: 10.3987/COM-94-S26.

Somei M., Iwaki T., Yamada F., Tanaka Yo., Shigenobu K., Koike K., Suzuki N., Hattori A. The Ideal Synthetic Method Aimed at the Leads for an α2-Blocker, an Inhibitor of Blood Platelet Aggregation, and an Anti-osteoporosis Agent. Heterocycles. 2006. V. 68. N 8. P. 1565–1569. DOI: 10.3987/COM-06-10771.

Eckardt N. A. Induction of Phytoalexin Biosynthesis: WRKY33 Is a Target of MAPK Signaling. Plant Cell. 2011. V. 23. P. 1190. DOI: 10.1105/tpc.111.230413.

Tomakinian T., Kouklovsky C., Vincent G. Investigation of the Synthesis of Benzofuroindolines from N-Hydroxyindoles: An O-Arylation/[3,3]-Sigmatropic Rearrangement Sequence. Synlett. 2015. V. 26. N 9. P. 1269-1275. DOI: 10.1055/s-0034-1380346.

Hafensteiner B.D., Escribano M., Petricci E., Baran Ph.S. An improved synthesis of α,β-unsaturated nitrones relevant to the stephacidins and analogs thereof. Bioorg. & Med. Chem. Lett. 2009. V. 19. N 14. P. 3808–3810. DOI: 10.1016/j.bmcl.2009.04.045.

Usotseva N.V., Bykova V.V., Kormilitsyn N.M., Ananieva G.A., Maizlish V.E. The dependence of lyotropic mesomorphism and intermolecular interactions of the carboxyphthalocyanine derivatives on the metal nature. Nuovo Cimento Sec. Ital. Fis. D. 1990. V. 12D. N 9. Р. 1237-1242. DOI: 10.1007/BF02450389.

Bykova V.V., Usol’tseva N.V., Anan’eva G.А., Shaposhnikov G.P., Maizlish V.E. Mezomorfizm tetra-4-alkoksi- и tetre-4-ariloksizameshchennyx aryloxy-substituted ptalocianinov medi. Izv. AN. Seriya fizicheskaya. 1998. V. 62. N 8. P. 1647-1651 (in Russian).

Schubert U., Lorenz A., Kundo N., Stuchinskaya T., Gogina L., Salanov A., Zaikovskii V., Maizlish V., Shaposhnikov G.P. Cobalt Phthalocyanine Derivatives Supported on TiO2 by Sol-Gel Processing. Part 1: Preparation and Microstructure. Chem. Ber. 1997. V. 130. N 11. Р.1585-1589. DOI: 10.1002/cber.19971301106.

Stuchinskaya T., Kundo N., Gogina L., Schubert U., Lorenz A., Maizlish V. Cobalt Phthalocyanine Derivatives Supported on TiO2 by Sol-Gel Processing. Part 2: Activity in Sulfide and Ethanethiol Oxidation. J. Mol. Catal. 1999. V. 140.

N 3. Р. 235-240. DOI: 10.1016/S1381-1169(98)00239-8.

Shaposhnikov G.P., Kulinich V.P., Maizlish V.E. Modified phthalocyanines and their structural analogies. М.: Krasand. 2012. 480 p. (in Russian).

Опубликован
2017-05-12
Как цитировать
Chirkova, Z. V. (2017). СИНТЕЗ N-ГИДРОКСИИНДОЛОВ. ИЗВЕСТИЯ ВЫСШИХ УЧЕБНЫХ ЗАВЕДЕНИЙ. СЕРИЯ «ХИМИЯ И ХИМИЧЕСКАЯ ТЕХНОЛОГИЯ», 60(4), 4-20. https://doi.org/10.6060/tcct.2017604.5560
Раздел
Обзорные статьи