Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines

Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines Научная публикация

Журнал

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Вых. Данные

Год: 2019, Том: 17, Номер: 6, Страницы: 1442-1454 Страниц : 13 DOI: 10.1039/c8ob03126f

Авторы

Motornov Vladimir A. ^1,2 , Tabolin Andrey A. ¹ , Nelyubina Yulia V. ³ , Nenajdenko Valentine G. ⁴ , Ioffe Sema L. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, Russia
2	Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow 125047, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow, Russia
4	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia

A general method for the synthesis of substituted indolizines by copper(II) acetate-promoted oxidative [3 + 2]-annulation of α-fluoronitroalkenes with in situ generated pyridinium ylides was developed. Application of the copper(II) acetate–2,6-lutidine system provides efficient access to various 1-fluoroindolizines in up to 81% yield. Both electron-rich and electron-deficient nitroalkenes as well as different pyridinium and isoquinolinium salts can be involved in the reaction. Moreover, it was found that copper-mediated annulation is applicable for other α-substituted (alkyl, chloro, and ester) nitroalkenes giving rise to the corresponding indolizines. First synthesis of monofluorinated [3,2,2]cyclazines was demonstrated via oxidative annulation of 3-unsubstituted fluoroindolizines with diethyl acetylene dicarboxylate.

Motornov V.A. , Tabolin A.A. , Nelyubina Y.V. , Nenajdenko V.G. , Ioffe S.L.
Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines
Organic & Biomolecular Chemistry. 2019. V.17. N6. P.1442-1454. DOI: 10.1039/c8ob03126f WOS Scopus OpenAlex

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