Sciact
  • EN
  • RU

Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif Научная публикация

Журнал Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353
Вых. Данные Год: 2019, Том: 55, Номер: 10, Страницы: 943-955 Страниц : 13 DOI: 10.1007/s10593-019-02561-y
Ключевые слова alkynyl ketones; ethynyl anthranilates; hydrazines; pyrazoles; cyclization; X-ray structural analysis
Авторы Savel'ev Viktor A. 1 , Kotova Anna A. 1,2 , Rybalova Tatyana, V 1,2 , Shults Elvira E. 1,2
Организации
1 (Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, 1 Pirogova St, Novosibirsk 630090, Russia

Реферат: An effective method was developed for the synthesis of 1,3,5-trisubstituted pyrazoles by using acetylenic ketones, obtained from ethyl 5-ethynylanthranilate, in reactions with substituted hydrazines and hydrazides. It was shown that the cyclization of ethyl 5-(3-aryl-3-oxopropinyl)- anthranilates with arylhydrazines proceeded regioselectively and led to the formation of 1,3,5-trisubstituted pyrazoles containing an anthranilate moiety at the position C-3. Significant deterioration of regioselectivity was observed in the reactions of ethyl 5-(3-aryl-3-oxopropinyl)anthranilates with N-methyl- and N-tert-butylhydrazines. The initial products formed in reactions of ethyl 5-[3-(4-fluorophenyl)-3-oxopropinyl]anthranilate with benzoyl and isonicotinoyl hydrazides were 5-hydroxypyrazolines, which underwent dehydration in the presence of pyridine and thionyl chloride in benzene, giving the respective 1,3,5-trisubstituted pyrazoles.
Библиографическая ссылка: Savel'ev V.A. , Kotova A.A. , Rybalova T.V. , Shults E.E.
Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif
Chemistry of Heterocyclic Compounds. 2019. V.55. N10. P.943-955. DOI: 10.1007/s10593-019-02561-y WOS Scopus РИНЦ
Даты:
Опубликована в печати: 1 окт. 2019 г.
Опубликована online: 19 окт. 2019 г.
Идентификаторы:
Web of science WOS:000491552200004
Scopus 2-s2.0-85074567850
РИНЦ 41701274
OpenAlex W2980554247
Альметрики: