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Some New Information on the Formation of Substituted 4-Amino-1-Substituted Phenyl-1H-Pyrazoles from beta-Enaminones and Diazonium Tetrafluoroborates
Authors: Šimůnek Petr | Macháček Vladimír | Svobodová Markéta | Růžička Aleš
Year: 2011
Type of publication: článek v odborném periodiku
Name of source: Journal of Heterocyclic Chemistry
Publisher name: Wiley-Blackwell
Page from-to: 780-786
Titles:
Language Name Abstract Keywords
cze Nové poznatky o tvorbě substituovaných 4-amino-1-subst.fenyl-1H-pyrazolů z beta-Enaminonů a diazonium-tetrafluoroborátů Při reakci 2-methyl-, 3-ethoxykarbonyl, a 4-ethoxykarbonylbenzendiazonium- tetrafluoroborátu s 1-cyklopropyl-3-fenylaminohex-2-en-1-onem vznikají 3-cyklopropylkarbonyl-1-(subst.fenyl)-5-ethyl-4-fenylamino-1H-pyrazoly. Na druhé straně reakce 1-cyklopropyl-3-fenylaminohex-2-en-1-onu a 5-methylaminohept-4-en-3-onu se stericky náročnějším 2-ethoxykarbonylbenzendiazonium-tetrafluoroborátem neposkytuje odpovídající pyrazoly ale možné intermediáty na cestě k pyrazolům: 1-cyklopropyl-3-fenyliminohexan-1,2,4-trion 2,4-bis(2-ethoxykarbonylfenylhydrazon) a 3-methyliminoheptan-2,4,5-trion 2,4-bis(2-ethoxykarbonylfenylhydrazon). Všechny sloučeniny byly identifikovány 1H- a 13C-NMR spektry. Struktura 1-cyklopropyl-3-fenyliminohexan-1,2,4-trionu 2,4-bis(2-ethoxykarbonylfenylhydrazonu) byla potvrzena 15N-NMR spektrem a X-ray. Bis(2-ethoxykarbonylfenylhydrazony) vykazují atropoisomerii. X-ray;NMR;azo produkty
eng Some New Information on the Formation of Substituted 4-Amino-1-Substituted Phenyl-1H-Pyrazoles from beta-Enaminones and Diazonium Tetrafluoroborates Upon reaction of 2-methyl-, 3-ethoxycarbonyl, and 4-ethoxycarbonylbenzenediazonium tetrafluoroborate with 1-cyclopropyl-3-phenylaminohex-2-en-1-one 3-cyclopropylcarbonyl-1-(substituted phenyl)-5-ethyl-4-phenylamino-1H-pyrazoles are formed. On the other hand, the reaction of 1-cyclopropyl-3-phenylaminohex-2-en-1-one and 5-methylaminohept-4-en-3-one with sterically more demanding 2-ethoxycarbonylbenzenediazonium tetrafluoroborate does not give the corresponding pyrazoles but the probable intermediates on the route to the pyrazoles: 1-cyclopropyl-3-phenyliminohexane-1,2,4-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone) and 3-methyliminoheptane-2,4,5-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone), respectively. All the compounds were identified on the basis of 1H-/13C-NMR spectra. The structure of 1-cyclopropyl-3-phenyliminohexane-1,2,4-trione 2,4-bis(2-ethoxycarbonylphenylhydrazone) was confirmed by 15N-NMR spectra and X-ray. The bis(2-ethoxycarbonylphenylhydrazones) were found to show atropoisomerism. AZO COUPLING PRODUCTS; X-RAY; NEUTRON-DIFFRACTION; BOND LENGTHS;TAUTOMERISM;SALTS;NMR;BENZOYLACETONE DERIVATIVEs

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