Synthesis of carbonylchromium complexes of benzimidazole and quinoxaline derivatives

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Two approaches to the preparation of chromium complexes of condensed heterocyclic compounds bearing two nitrogen atoms are approved. The reactions of benzimidazole (L1) and 2-methylbenzimidazole (L2) with triammine(tricarbonyl)chromium (I) give the corresponding pentacarbonylchromium derivatives [(η1-C7H6N2)]Cr(CO)5 (II) and [2-Me-(η1-C7H5N2)]Cr(CO)5 (III) characterized by the nitrogen–chromium σ-bond, and ammine(pentacarbonyl)chromium (Cr(NH3)(CO)5, IV) is formed as a by-product. Analogous reactions involving 1,2,3,4-tetrahydroquinoxaline (L3) and 3-phenyl-1,2-dihydroquinoxaline (L4) afford tricarbonylchromium π-complexes [(η6-C6H4)C2H6N2)]Cr(CO)3 (V) and [3-Ph-(η6-C6H4)C2H3N2)]Cr(CO)3 (VI), respectively. The condensations of (η6-ortho-phenylenediamine)tricarbonylchromium (VII) with benzaldehyde and of ortho- phenylenediamine with (η6-benzaldehyde)tricarbonylchromium (VIII) afford acyclic compounds (azomethines [PhCH=N(η6-C6H4)NH2]Cr(CO)3 (IX) and [(η6-Ph)CH=NC6H4NH2]Cr(CO)3 (X), respectively), whereas the reaction of acetaldehyde with complex VII gives a mixture of heterocyclic products: exo-[1,3-bis-(C2H4OEt)-2-Me-(η6-C6H4)CHN2]Cr(CO)3 (XI) and endo-[1,3-bis-(C2H4OEt)-2-Me-(η6-C6H4)CHN2]Cr(CO)3 (XII). The spectral characteristics of the synthesized compounds are studied, and their purity and individual character are proved. The molecular structures of complexes III and XI are determined by XRD (CIF files CCDC nos. 2245463 (III) and 2362231 (XI)).

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作者简介

A. Grishin

National Research Lobachevsky State University of Nizhny Novgorod

Email: zarovkinan@mail.ru
俄罗斯联邦, Nizhny Novgorod

E. Sazonova

National Research Lobachevsky State University of Nizhny Novgorod

Email: zarovkinan@mail.ru
俄罗斯联邦, Nizhny Novgorod

N. Somov

National Research Lobachevsky State University of Nizhny Novgorod

Email: zarovkinan@mail.ru
俄罗斯联邦, Nizhny Novgorod

S. Baryshnikova

Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences

Email: zarovkinan@mail.ru
俄罗斯联邦, Nizhny Novgorod

N. Grishina

National Research Lobachevsky State University of Nizhny Novgorod

编辑信件的主要联系方式.
Email: zarovkinan@mail.ru
俄罗斯联邦, Nizhny Novgorod

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2. Scheme 1

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3. Fig. 1. Molecular structure of 2-methyl-(η1-benzimidazole)chromopentacarbonyl (III). Thermal ellipsoids are shown with 80% probability. Hydrogen atoms are not shown.

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4. Scheme 2

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5. Scheme 3

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6. Scheme 4

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7. Fig. 2. Molecular structure of 1,3-bis-(1-ethoxyethyl)-2-methyl-(η6-2,3-dihydrobenzimidazole)chromium tricarbonyl (XI). Thermal ellipsoids are shown with 80% probability. Hydrogen atoms are not shown.

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8. Scheme 5

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