Synthesis of trifluoromethyl-​substituted pyrazolo[4,​3-​c]​pyridines - sequential versus multicomponent reaction approach

Barbara Palka; Angela Di Capua; Maurizio Anzini; Gyte Vilkauskaite; Algirdas Sackus; Wolfgang Holzer

doi:10.3762/bjoc.10.183

Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines - sequential versus multicomponent reaction approach

Barbara Palka, Angela Di Capua, Maurizio Anzini, Gyte Vilkauskaite, Algirdas Sackus, Wolfgang Holzer (Corresponding author)

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compds. in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations (1H, 13C, 15N and 19F) were undertaken with all obtained products.

Original language	English
Pages (from-to)	1759-1764
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	10
DOIs	https://doi.org/10.3762/bjoc.10.183
Publication status	Published - 31 Jul 2014

Austrian Fields of Science 2012

104015 Organic chemistry
301207 Pharmaceutical chemistry

Keywords

microwave-assisted reactions
multicomponent reactions
NMR (H-1; C-13; N-15; F-19)
Sonogashira coupling
trifluoromethylpyrazoles
MEDICINAL CHEMISTRY
RING-CLOSURE
N-OXIDES
HETEROCYCLES
INHIBITOR
FLUORINE
Microwave-assisted reactions
Multicomponent reactions
Trifluoromethylpyrazoles

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10.3762/bjoc.10.183Licence: Other

http://phaidra.univie.ac.at/o:454132Licence: Other

Cite this

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title = "Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines - sequential versus multicomponent reaction approach",

abstract = "A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compds. in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations (1H, 13C, 15N and 19F) were undertaken with all obtained products.",

keywords = "microwave-assisted reactions, multicomponent reactions, NMR (H-1; C-13; N-15; F-19), Sonogashira coupling, trifluoromethylpyrazoles, MEDICINAL CHEMISTRY, RING-CLOSURE, N-OXIDES, HETEROCYCLES, INHIBITOR, FLUORINE, Microwave-assisted reactions, Multicomponent reactions, Trifluoromethylpyrazoles",

author = "Barbara Palka and {Di Capua}, Angela and Maurizio Anzini and Gyte Vilkauskaite and Algirdas Sackus and Wolfgang Holzer",

year = "2014",

month = jul,

day = "31",

doi = "10.3762/bjoc.10.183",

language = "English",

volume = "10",

pages = "1759--1764",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "BEILSTEIN-INSTITUT",

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T1 - Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines - sequential versus multicomponent reaction approach

AU - Palka, Barbara

AU - Di Capua, Angela

AU - Anzini, Maurizio

AU - Vilkauskaite, Gyte

AU - Sackus, Algirdas

AU - Holzer, Wolfgang

PY - 2014/7/31

Y1 - 2014/7/31

N2 - A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compds. in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations (1H, 13C, 15N and 19F) were undertaken with all obtained products.

AB - A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compds. in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations (1H, 13C, 15N and 19F) were undertaken with all obtained products.

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KW - HETEROCYCLES

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KW - Multicomponent reactions

KW - Trifluoromethylpyrazoles

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DO - 10.3762/bjoc.10.183

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines - sequential versus multicomponent reaction approach

Abstract

Austrian Fields of Science 2012

Keywords

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Cite this

Synthesis of trifluoromethyl-​substituted pyrazolo[4,​3-​c]​pyridines - sequential versus multicomponent reaction approach

Abstract

Austrian Fields of Science 2012

Keywords

Access to Document

Other files and links

Fingerprint

Cite this

Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines - sequential versus multicomponent reaction approach