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

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Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif. / Savel’ev, Viktor A.; Kotova, Anna A.; Rybalova, Tatyana V. et al.

In: Chemistry of Heterocyclic Compounds, Vol. 55, No. 10, 01.10.2019, p. 943-955.

Research output: Contribution to journal › Article › peer-review

Harvard

Savel’ev, VA, Kotova, AA, Rybalova, TV & Shults, EE 2019, 'Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif', Chemistry of Heterocyclic Compounds, vol. 55, no. 10, pp. 943-955. https://doi.org/10.1007/s10593-019-02561-y

APA

Savel’ev, V. A., Kotova, A. A., Rybalova, T. V., & Shults, E. E. (2019). Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif. Chemistry of Heterocyclic Compounds, 55(10), 943-955. https://doi.org/10.1007/s10593-019-02561-y

Vancouver

Savel’ev VA, Kotova AA, Rybalova TV, Shults EE. Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif. Chemistry of Heterocyclic Compounds. 2019 Oct 1;55(10):943-955. doi: 10.1007/s10593-019-02561-y

Author

Savel’ev, Viktor A. ; Kotova, Anna A. ; Rybalova, Tatyana V. et al. / Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif. In: Chemistry of Heterocyclic Compounds. 2019 ; Vol. 55, No. 10. pp. 943-955.

BibTeX

@article{765f7310925b4902a738d3c141861c5b,

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

abstract = "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.",

keywords = "alkynyl ketones, cyclization, ethynyl anthranilates, hydrazines, pyrazoles, X-ray structural analysis, CATALYSIS, DESIGN, PALLADIUM COMPLEXES, MODULATORS, PYRIMIDINES, CRYSTAL-STRUCTURES, PATHWAY, ACETYLENIC KETONES, DERIVATIVES",

author = "Savel{\textquoteright}ev, {Viktor A.} and Kotova, {Anna A.} and Rybalova, {Tatyana V.} and Shults, {Elvira E.}",

note = "Publisher Copyright: {\textcopyright} 2019, Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2019",

month = oct,

day = "1",

doi = "10.1007/s10593-019-02561-y",

language = "English",

volume = "55",

pages = "943--955",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "10",

}

RIS

TY - JOUR

T1 - Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif

AU - Savel’ev, Viktor A.

AU - Kotova, Anna A.

AU - Rybalova, Tatyana V.

AU - Shults, Elvira E.

PY - 2019/10/1

Y1 - 2019/10/1

N2 - 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.

AB - 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.

KW - alkynyl ketones

KW - cyclization

KW - ethynyl anthranilates

KW - hydrazines

KW - pyrazoles

KW - X-ray structural analysis

KW - CATALYSIS

KW - DESIGN

KW - PALLADIUM COMPLEXES

KW - MODULATORS

KW - PYRIMIDINES

KW - CRYSTAL-STRUCTURES

KW - PATHWAY

KW - ACETYLENIC KETONES

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85074567850&partnerID=8YFLogxK

U2 - 10.1007/s10593-019-02561-y

DO - 10.1007/s10593-019-02561-y

M3 - Article

AN - SCOPUS:85074567850

VL - 55

SP - 943

EP - 955

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 10

ER -

ID: 22364141