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

Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2019, Volume: 55, Number: 10, Pages: 943-955 Pages count : 13 DOI: 10.1007/s10593-019-02561-y

Tags

alkynyl ketones; ethynyl anthranilates; hydrazines; pyrazoles; cyclization; X-ray structural analysis

Authors

Savel'ev Viktor A. ¹ , Kotova Anna A. ^1,2 , Rybalova Tatyana, V ^1,2 , Shults Elvira E. ^1,2

Affiliations

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

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.

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

Published print:	Oct 1, 2019
Published online:	Oct 19, 2019

Web of science	WOS:000491552200004
Scopus	2-s2.0-85074567850
Elibrary	41701274
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