Synthesis, molecular structure, electrochemistry and DFT study of a ferrocenyl-substituted 4-quinazolinone and related heterocycles

Kód výsledku v IS VaVaI

RIV/00216208:11310/13:10134332 - isvavai.cz

Výsledek na webu

http://dx.doi.org/10.1039/c3nj00182b

DOI - Digital Object Identifier

10.1039/c3nj00182b

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis, molecular structure, electrochemistry and DFT study of a ferrocenyl-substituted 4-quinazolinone and related heterocycles

Popis výsledku v původním jazyce

2-Ferrocenyl-4(3H)-quinazolinone (2) was obtained by acylation of 2-aminobenzoic amide with ferrocenecarbonyl chloride (FcCOCl) and subsequent base-catalysed cyclisation of the intermediate 2-(ferrocenecarboxamido)benzamide (1). The related benzoxazin-4-one (4) was obtained analogously (though in one step) from FcCOCl and 2-aminobenzoic acid. Compounds 2 and 4 were thionated with P2S5 to give the corresponding ferrocenylated 4(3H)-quinazoline thione (3), and a mixture of benzothiazine-4-thione (5) and benzothiazine-4-one (6, major), respectively. Attempts to prepare 3-amino-2-ferrocenyl-4(3H)-quinazolinone from 4 and hydrazine hydrate failed. The reaction gave only 2-(ferrocenecarboxamido)benzohydrazide (7), which reacted with 2-chloro-1,3-dimethylimidazolidinium chloride to afford a mixture of cyclic and open (major) condensation products, both bearing the 1,3-dimethylimidazolidin-2-ylidene terminal group (8 and 9). All compounds were characterised by spectroscopic methods and the mol

Název v anglickém jazyce

Synthesis, molecular structure, electrochemistry and DFT study of a ferrocenyl-substituted 4-quinazolinone and related heterocycles

Popis výsledku anglicky

2-Ferrocenyl-4(3H)-quinazolinone (2) was obtained by acylation of 2-aminobenzoic amide with ferrocenecarbonyl chloride (FcCOCl) and subsequent base-catalysed cyclisation of the intermediate 2-(ferrocenecarboxamido)benzamide (1). The related benzoxazin-4-one (4) was obtained analogously (though in one step) from FcCOCl and 2-aminobenzoic acid. Compounds 2 and 4 were thionated with P2S5 to give the corresponding ferrocenylated 4(3H)-quinazoline thione (3), and a mixture of benzothiazine-4-thione (5) and benzothiazine-4-one (6, major), respectively. Attempts to prepare 3-amino-2-ferrocenyl-4(3H)-quinazolinone from 4 and hydrazine hydrate failed. The reaction gave only 2-(ferrocenecarboxamido)benzohydrazide (7), which reacted with 2-chloro-1,3-dimethylimidazolidinium chloride to afford a mixture of cyclic and open (major) condensation products, both bearing the 1,3-dimethylimidazolidin-2-ylidene terminal group (8 and 9). All compounds were characterised by spectroscopic methods and the mol

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CA - Anorganická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

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Svazek periodika

37

Číslo periodika v rámci svazku

7

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

12

Strana od-do

2019-2030

Kód UT WoS článku

000320466600024

EID výsledku v databázi Scopus

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