Mononuclear nickel(II) complexes with arylhydrazones of acetoacetanilide and their catalytic activity in nitroaldol reaction

The new mononuclear nickel(II) complexes [Ni(HL1)(H2O)2(CH3OH)] (1, NaH2L1 = sodium (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzenesulfonate) and [Ni(H2L2)2(H2O)4] [(CH3)2S[dbnd]O)2] (2, H3L2 = (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzoic acid) were synthesized and characterized by IR and ESI-MS spectroscopies, elemental and X-ray crystal structural analyses. Both compounds 1 and 2 act as homogenous catalysts for the diastereoselective nitroaldol (Henry) reaction of aliphatic and aromatic aldehydes with nitroethane in different solvents such as acetonitrile, methanol or water. Complex 1 was found to be the more efficient catalyst for the Henry reaction in aqueous medium, providing β-nitroalcohols with good yields (67–82%) and diastereoselectivities (syn/anti 59:41–70:30). © 2017 Elsevier B.V.

Authors
Gurbanov A.V. 1, 2, 3 , Huseynov F.E. 3, 4 , Mahmoudi G. 5 , Maharramov A.M.2 , Guedes Da Silva F.C. , Mahmudov K.T. 1, 3, 4 , Pombeiro A.J.L.1
Journal
Inorganica Chimica Acta
Language
English
Pages
197-201
Status
Published
Link
External link
DOI
10.1016/j.ica.2017.09.037
Volume
469
Year
2018
Organizations
  • 1 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049-001, Portugal
  • 2 Organic Chemistry Department, Baku State University, Z. Xalilov Str. 23, Baku, Az 1148, Azerbaijan
  • 3 Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya Str., Moscow, 117198, Russian Federation
  • 4 Department of Ecology and Soil Sciences, Baku State University, Z. Xalilov Str. 23, Baku, Az 1148, Azerbaijan
  • 5 Department of Chemistry, Faculty of Science, University of Maragheh, P.O. Box 55181-83111, Maragheh, Iran
Keywords
Arylhydrazones of acetoacetanilide; Henry reaction; Ni(II) complexes
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/7351/
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