Facile Synthesis and Structural Characterization by NMR,ESI–MS/MS and DFT Calculations of New (E)‐6‐[2‐Ferrocenylalkylidenehydrazino]nicotinic Hydrazides and Their (E)‐Ferrocenyl‐pyrazolyl‐pyridine Heterocyclic System |
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| Authors: | Liliane M. F. Porte Gisele R. Paim Thiago G. Schwanz Alexandre R. Meyer Helio G. Bonacorso Marcos A. P. Martins Nilo Zanatta |
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| Affiliation: | 1. Núcleo de Química de Heterociclos – NUQUIMHE, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil;2. Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil;3. Núcleo de Análises e Pesquisas Organicas – NAPO, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil |
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| Abstract: | This paper reports a facile and convenient access by a conventional thermal procedure in ethanol as solvent to a new examples of (E)‐6‐[2‐ferrocenylalkylidenehydrazino]nicotinic hydrazides ( 3 ) (53–72%) from the quimioselective reactions of 6‐hydrazinonicotinc hydrazide ( 1 ) with acylferrocenes ( 2 ), where acyl = formyl and acetyl. Subsequently, cyclocondensation reactions of ferrocenylalkylidene hydrazones ( 3 ) with 4‐R1‐4‐alkoxy‐1,1,1‐trifluoroalk‐3‐en‐2‐ones ( 4 ), where R1 = Me, Ph, 2‐Furyl, to obtain new six heterocyclic derivatives as (E)‐pyrazolyl‐pyridinohydrazones ( 5 ) (58–63%), are also presented. The structures of these new heterocyclic compounds 5 containing an organometallic unit were characterized and studied by NMR, ESI–MS/MS techniques. DFT calculations were also employed to assign the E configuration for compounds 3 and 5 . |
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