Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles

Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles Full article

Journal

New Journal of Chemistry
ISSN: 1369-9261 , E-ISSN: 1144-0546

Output data

Year: 2022, Volume: 46, Number: 9, Pages: 4134-4141 Pages count : 8 DOI: 10.1039/d1nj05332a

Authors

Motornov Vladimir A. ¹ , Tabolin Andrey A. ¹ , Ioffe Sema L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991, Russia

A facile synthesis of [5,5]-annulated N-fused heterocycles – pyrrolo[2,1-b]thiazoles and pyrrolo[1,2-b]indazoles via oxidative [3+2]-annulation between nitroalkenes and azolium ylides in the presence of copper(II) was developed. The reaction proceeds in mild conditions with the copper(II) trifluoroacetate/2,6-lutidine system. The method is applicable to a broad range of nitroalkenes and azolium salts, providing the target N-fused heterocycles in moderate to good yields. In the case of α-fluoronitroalkenes, unique fluorinated derivatives were accessed via this methodology.

Motornov V.A. , Tabolin A.A. , Ioffe S.L.
Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles
New Journal of Chemistry. 2022. V.46. N9. P.4134-4141. DOI: 10.1039/d1nj05332a WOS Scopus OpenAlex

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