Journal of Siberian Federal University. Chemistry / Synthesis of nitrosoand amino-N-adamantylpirazoles

Full text (.pdf)
Issue
Journal of Siberian Federal University. Chemistry. 2011 4 (3)
Authors
Frolenko, Timofey A.; Semichenko, Elena S.; Melnikova, Maria G.; Gavrilova, Natalia A.; Suboch, George A.
Contact information
Frolenko, Timofey A. : Siberian State Technological University , 82 Mira, Krasnoyarsk, 660049 Russia; Semichenko, Elena S. : Siberian State Technological University , 82 Mira, Krasnoyarsk, 660049 Russia , e-mail: ; Melnikova, Maria G. : Siberian State Technological University , 82 Mira, Krasnoyarsk, 660049 Russia; Gavrilova, Natalia A. : Siberian State Technological University , 82 Mira, Krasnoyarsk, 660049 Russia; Suboch, George A. : Siberian State Technological University , 82 Mira, Krasnoyarsk, 660049 Russia
Keywords
1-(1-adamantyl)-3,5-dimethyl-4-nitroso-1H-pyrazole; 1-(1-adamantyl)-5-methyl-4- nitroso-3-phenyl-1H-pyrazole; 1-(1-adamantyl)-3-methyl-4-nitroso-1H-pyrazole; 2-hydroxyimino- 1,3-diketone; 3-hydroxyimino-2,4-pentanedione; 2-(hydroxyimino)-3-oxobutanal
Abstract

1-(1-Адамантил)-3,5-диметил-4-нитрозо-1H-пиразол и 1-(1-адамантил)-5-метил-4-нитрозо- 3-фенил-1H-пиразол синтезированы циклоконденсацией 2-гидроксимино-1,3-дикетонов с дигидрохлоридом адамантилгидразина. 1-(1-Адамантил)-3-метил-4-нитрозо-1H-пиразол получен циклоконденсацией дигидрохлорида адамантилгидразина с продуктом нитрозирования 4,4-диметоксибутан-2-она в кислой среде. При восстановлении синтезированных 4-нитрозопиразолов гидразин-гидратом в присутствии катализатора Pd/C получены соответствующие 4-аминопиразолы.

Synthesis of 1-(1-adamantyl)-3,5-dimethyl-4-nitroso-1H-pyrazole and 1-(1-adamantyl)-5-methyl-4- nitroso-3-phenyl-1H-pyrazole done by the cyclocondensation of 2-hydroxyimino-1,3-diketones and adamantylhydrazine dihydrochloride. Synthesis of 1-(1-adamantyl)-3-methyl-4-nitroso-1H-pyrazole done by reaction of unstable 2-hydroxyimino-3-oxobutanal and adamantylhydrazine hydrochloride. 2-Hydroxyimino-3-oxobutanal obtained by nitrosation of 4,4-dimethoxybutan-2-one in an acid medium. The 2-(hydroxyimino)-3-oxobutanal was injected into the cyclocondensation without isolation from the reaction mixture.1-(1-Аdamantyl)-4-amino-1H-pyrazoles were synthesized through the chemical reduction of synthesized 4-nitrosopyrazoles with hydrazine hydrate in the presence of Pd/C.

Pages
301-306
Paper at repository of SibFU
https://elib.sfu-kras.ru/handle/2311/2598