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Elsevier, Tetrahedron, 45(71), p. 8622-8627

DOI: 10.1016/j.tet.2015.09.020

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Co(II)-mediated synthesis of 2-carbamimidoylbenzoates and isoindole-1,3-diaminates

Journal article published in 2015 by Maximilian N. Kopylovich ORCID, Matti Haukka, Kamran T. Mahmudov ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Phthalonitrile, acetoxime and cobalt(II) nitrate hexahydrate are combined in acetone with formation of stable and easy to handle Co(II) complex [Co{C6H4C(NH2)NC(ONCMe2)2}2](NO3)2 (1). Interaction of 1 with excess alcohols ROH (also used as solvents) and 2 equiv of (NH4)2S leads, in one-step, to alkyl 2-carbamimidoylbenzoate nitrates [C6H4COOR{2-C(NH2)2}]NO3 [R=CH3, C2H5, C3H7, CH(CH3)2]. Similarly, N1,N3-dialkyl-1H-isoindole-1,3-diaminate nitrates [C6H4C(NR′)NC(NR′)]NO3 [R=C3H7, C4H9, C(CH3)3, CH2CH2OH, CH2CH2SC2H5) can be directly produced from 1 by its reaction with 4 equiv of amines and 2 equiv of (NH4)2S in alcoholic media.