Фураны в синтезе азагетероциклов (1098257), страница 69
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Предложен и успешно реализован способ решения проблемы низкой эффективности процесса при наличии стерических препятствий циклизации с образованием азепинового цикла, основанный на изучении механизмаэтих реакций, в том числе с использованием неэмпирических квантово-химическихрасчётов высокого уровня.10. Разработан метод получения из производных 2-(2-аминофенил)фурана соответствующих 2-(2-оксоалкил)индолов, основанный на использовании необычной реакционной способности фуранов как синтетических эквивалентов 1,3-дикетонов.342Список литературы1.Introduction to Chemicals from Biomass / ed. J.
H. Clark, F. E. I. Deswante – Wiley –Chichester – 2008. – 198 pp.2.Corma A. Chemical Routes for the Tranformation of Biomass into Chemicals / A.Corma, S. Iborra, A. Velty // Chem. Rev. – 2007. – V. 107. – № 6. – P. 2411–2502.3.Serrano-Ruiz J. C. Transformations of biomass-derived platform molecules: from highadded-value chemicals to fuels via aqueous-phase processing / J. C.
Serrano-Ruiz, R.Luque, A. Sepulveda-Escribano // Chem. Soc. Rev. – 2011. – V. 40. – № 11. – P. 5266–5281.4.Gallezot P. Conversion of biomass to selected chemical products / P. Gallezot // Chem.Soc. Rev. – 2012. – V. 41. – № 4. – P. 1538–1558.5.Besson M. Conversion of Biomass into Chemicals over Metal Catalysts / M. Besson, P.Gallezot, C. Pinel // Chem. Rev. – 2014. – V. 114.
– № 3. – P. 1827–1870.6.Straathof A. J. J. Transformation of Biomass into Commodity Chemicals Using Enzymesor Cells / A. J. J. Straathof // Chem. Rev. – 2014. – V. 114. – № 3. – P. 1871–1908.7.Bozell J. J. Technology development for the production of biobased products frombiorefinery carbohydrates – the US Department of Energy’s “Top 10” revisited / J. J.Bozell, G. R. Petersen // Green Chem. – 2010.
– V. 12. – № 4. – P. 539–554.8.van Putten R.-J. Hydroxymethylfurfural, A Versatile Platform Chemical Made fromRenewable Resources / R.-J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra,H. J. Heeres, J. G. de Vries // Chem. Rev. – 2013. – V. 113. – № 3.
– P. 1499–1597.9.Piancatelli G. A useful preparation of 4-substituted 5-hydroxy-3-oxocyclopentene / G.Piancatelli, A. Scettri, S. Barbadoro // Tetrahedron Lett. – 1976. – V. 17. – № 39. –P. 3555–3558.10.Piutti C. The Piancatelli Rearrangement: New Applications for an Intriguing Reaction /C. Piutti, F. Quartieri // Molecules – 2013. – V. 18. – № 10. – P.
12290–12312.11.Achmatowicz O. Synthesis of methyl 2,3-dideoxy-alk-2-enopyranosides from furan compounds: A general approach to the total synthesis of monosaccharides / O. Achmatowicz,P. Bukowski, B. Szechner, Z. Zwierzchowska, A. Zamojski // Tetrahedron – 1971. – V.27. – № 10. – P. 1973–1996.12.Ciufolini M. A.
Nitrogen Heterocycles from Furans: The Aza-Achmatowicz Reaction /M. A. Ciufolini, C. Y. W. Hermann, Q. Dong, T. Shimizu, S. Swaminathan, N. Xi //Synlett – 1998. – № 2. – P. 105–114.34313.Hirano K. Direct Synthesis of Fused Indoles by Gold-Catalyzed Cascade Cyclization ofDiynes / K. Hirano, Y. Inaba, N. Takahashi, M.
Shimano, S. Oishi, N. Fujii, H. Ohno // J.Org. Chem. – 2011. – V. 76. – № 5. – P. 1212–1227.14.Xia Y. Rhodium(II)-Catalyzed Cyclization of Bis(N-tosylhydrazone)s: An Efficient Approach towards Polycyclic Aromatic Compounds / Y. Xia, Z. Liu, Q. Xiao, P. Qu, R. Ge, Y.Zhang, J. Wang // Angew. Chem.
Int. Ed. – 2012. – V. 51. – № 23. – P. 5714–5717.15.Ito C. New Carbazole Alkaloids from Murraya eucrestifolia Hayata / C. Ito, H. Furukawa// Chem. Pharm. Bull. – 1990. – V. 38. – № 6. – P. 1548–1550.16.Lou S. Palladium/Tris(tert-butyl)phosphine-Catalyzed Suzuki Cross-Couplings in the Presence of Water / S. Lou, G. C. Fu // Adv. Synth. Catal. – 2010. – V. 352. – № 11-12.
– P.2081–2084.17.Zhu X. I-MCR-Ullmann cascade toward furo[2,3-b]indole scaffold / X. Zhu, X.-P. Xu, C.Sun, T. Chen, Z.-L. Shen, S.-J. Ji // Tetrahedron – 2011. – V. 67. – № 34. – P. 6375–6381.18.Cadogan J. I. G. The Reactivity of Organophosphorus Compounds. Part XIX. Reduction ofNitro-compounds by Triethyl Phosphite: a Convenient New Route to Carbazoles, Indoles,Indazoles, Triazoles, and Related Compounds / J. I. G. Cadogan, M. Cameron-Wood, R.K.
Mackie, R. J. G. Searle // J. Chem. Soc. – 1965. – № 4. – P. 4831–4837.19.Freeman A. W. Triphenylphosphine-Mediated Reductive Cyclization of 2-Nitrobiphenyls:A Practical and Convenient Synthesis of Carbazoles / A. W. Freeman, M. Urvoy, M. E.Criswell // J. Org. Chem. – 2005. – V. 70. – № 13.
– P. 5014–5019.20.Creencia E. C. Microwave-assisted Cadogan reaction for the synthesis of 2-aryl-2H-indazoles, 2-aryl-1H-benzimidazoles, 2-carbonylindoles, carbazole, amd phenazine / E. C. Creencia, M. Kosaka, T. Muramatsu, M. Kobayashi, T. Iizuka, T. Horaguchi // J. Heterocycl.Chem. – 2009. – V. 46. – № 6. – P. 1309–1317.21.Tanaka A. Synthesis of 4H-Furo[3,2-b]indole Derivatives. A New Heterocyclic Ring System / A. Tanaka, K. Yakushijin, S. Yoshina // J. Heterocycl.
Chem. – 1977. – V. 14. – № 6.– P. 975–979.22.Tanaka A. Synthesis of 4H-Furo[3,2-b]indole Derivatives. III. Preparation of 4H-Furo[3,2b]indole-2-carboxylic acid Derivatives / A. Tanaka, K. Yakushijin, S. Yoshina // J. Heterocycl. Chem. – 1979. – V. 16. – № 4. – P. 785–788.23.Sundberg R. J. Rearrangements and Ring Expansions during the Deoxygenation of β,βDisubstituted o-Nitrostyrenes / R. J. Sundberg, T. Yamazaki // J. Org. Chem.
– 1967. –V. 32. – № 2. – P. 290–294.34424.Krutošikova A. Reactions of ethyl 2-(nitrophenyl)-4H-furo[3,2-b]pyrrole-5-carboxylate /A. Krutošikova, J. Kovač, M. Dandarova, M. Veverka // Collect. Czech. Chem. Commun. –1979. – V. 44. – № 6. – P. 1805–1809.25.Korenova A. Synthesis and reactions of furocondensed systems containing indole skeleton/ A. Korenova, A. Krutošikova, M. Dandarova, J. Kovač // Collect.
Czech. Chem. Commun. – 1984. – V. 49. – № 6. – P. 1529–1535.26.Kralovičova E. Preparations and reactions of thieno[3,2-b]furan derivatives / E. Kralovičova, A. Krutošikova, J. Kovač // Collect. Czech. Chem. Commun. – 1986. – V. 51. – № 8.– P. 1685–1691.27.Korenova A. Synthesis and reactions of furo[3,2-c]pyridine derivatives / A.
Korenova, A.Krutošikova, J. Kovač, S. Celec // Collect. Czech. Chem. Commun. – 1987. – V. 52. – № 1.– P. 192–198.28.Tanaka A. Synthesis of 4H-Furo[3,2-b]indoles. II. Bromination, acylation and nitration of4H- and 4-benzoylfuro[3,2-b]indoles / A. Tanaka, K. Yakushijin, S. Yoshina // J. Heterocycl. Chem. – 1978. – V. 15. – № 1. – P. 123–125.29.Pudlo M.
First Suzuki-Miyaura type cross-coupling of ortho-azidobromobenzene witharylboronic acids and its application tot he synthesis of fused aromatic indole-heterocycles/ M. Pudlo, D. Csanyi, F. Moreau, G. Hajos, Z. Riedl, J. Sapi // Tetrahedron – 2007. –V. 63. – № 41.
– P. 10320–10329.30.Nakashima Y. Furo[3,2-b]indole Derivatives. I. Synthesis and Analgesic and Anti-inflammatory Activities of 4,6-Disubstituted-furo[3,2-b]indole-2-carboxamide Derivatives / Y.Nakashima, Y. Kawashima, F. Amanuma, K. Sota, A. Tanaka, T. Kameyama // Chem.Pharm. Bull. – 1984. – V. 32. – № 11. – P.
4271–4280.31.Nakashima Y. Furo[3,2-b]indole Derivatives. II. Synthesis and Analgesic and Anti-inflammatory Activities of 4-Alkoxycarbonyl-2-morpholinocarbonylfuro[3,2-b]indole Derivatives / Y. Nakashima, Y. Kawashima, M. Sato, S. Okuyama, F. Amanuma, K. Sota, T.Kameyama // Chem. Pharm. Bull. – 1985.
– V. 32. – № 12. – P. 5250–5257.32.Kawashima Y. Structure-Activity Studies of 4,6-Disubstituted 2-(Morpholinocarbonyl)furo[3,2-b]indole Derivatives with Analgesic and Antiinflammatory Activities / Y. Kawashima, F. Amanuma, M. Sato, S. Okuyama, Y. Nakashima, K. Sota, I. Moriguchi // J. Med.Chem. – 1986. – V.
29. – № 11. – P. 2284–2290.33.Katritzky A. R. A General and Facile Synthesis of Heterocyclo[b]-fused Carbazoles / A. R.Katritzky, L. Xie // J. Org. Chem. – 1995. – V. 60. – № 12. – P. 3707–3710.34.Lee P.-S. Aldimine-Directed Branched-Selective Hydroarylation of Styrenes / P.-S. Lee,N. Yoshikai // Angew. Chem. Int. Ed. – 2013.
– V. 52. – № 4. – P. 1240–1244.34535.Chunchatprasert L. A New Synthetic Route to Pyrrolo[3,2-b]carbazoles, 1H-Benzofuro[3,2-f]indoles and 1H-[1]Benzothieno[2,3-f]indoles / L. Chunchatprasert, K. R. N. Rao, P.V. R. Shannon // J. Chem. Soc. Perkin Trans. 1 – 1992. – № 14. – P. 1779–1783.36.Sureshbabu R. Lewis Acid Mediated One Pot Synthesis of Aryl/Heteroaryl Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/AromatizationReaction Sequence / R. Sureshbabu, V. Saravanan, V. Dhayalan, A.
K. Mohanakrishnan //Eur. J. Org. Chem. – 2011. – № 5. – P. 922–935.37.Dhayalan V. A Versatile Synthesis of Annulated Carbazole Analogs Involving a DominoReaction of Bromomethylindoles with Arenes/Heteroarenes / V. Dhayalan, J. A. Clement,R. Jagan, A. K. Mohanakrishnan // Eur. J.
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