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The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process

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The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process. / Beltran-Rodil, Sandra; Edwards, Michael G.; Pugh, David. S.; Reid, Mark; Taylor, Richard J. K.

In: Synlett, No. 4, D27509ST, 03.2010, p. 602-606.

Research output: Contribution to journalArticlepeer-review

Harvard

Beltran-Rodil, S, Edwards, MG, Pugh, DS, Reid, M & Taylor, RJK 2010, 'The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process', Synlett, no. 4, D27509ST, pp. 602-606. https://doi.org/10.1055/s-0029-1218521

APA

Beltran-Rodil, S., Edwards, M. G., Pugh, D. S., Reid, M., & Taylor, R. J. K. (2010). The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process. Synlett, (4), 602-606. [D27509ST]. https://doi.org/10.1055/s-0029-1218521

Vancouver

Beltran-Rodil S, Edwards MG, Pugh DS, Reid M, Taylor RJK. The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process. Synlett. 2010 Mar;(4):602-606. D27509ST. https://doi.org/10.1055/s-0029-1218521

Author

Beltran-Rodil, Sandra ; Edwards, Michael G. ; Pugh, David. S. ; Reid, Mark ; Taylor, Richard J. K. / The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process. In: Synlett. 2010 ; No. 4. pp. 602-606.

Bibtex - Download

@article{1e2041e98eb64ad9b5e9b3da25436778,
title = "The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process",
abstract = "Two consecutive tandem processes are described for the regioselective, two-step synthesis of 1,3,5-trisubstituted pyrazoles from alpha-hydroxyketones. The first, a tandem MnO2-mediated oxidation/Ramirez olefination reaction, provides a facile route to beta,beta-dibromo-enones. These valuable 1,3-dicarbonyl synthons can then be converted into 1,3,5-trisubstituted pyrazoles via a second tandem hydrazine condensation/Suzuki-Miyaura cross-coupling reaction. Using these procedures, a range of aryl and alkyl alpha-hydroxyketones have been transformed regioselectively into 1,3,5-trisubstituted pyrazoles.",
keywords = "tandem oxidation process, TOP, beta,beta-dibromo-enones, 1,3,5-trisubstituted pyrazoles, Suzuki-Miyaura, ONE-POT CONVERSION, OXIDATION PROCESSES, MANGANESE-DIOXIDE, KETONES, 1,1-DIBROMO-1-ALKENES, DERIVATIVES, ALKYNES",
author = "Sandra Beltran-Rodil and Edwards, {Michael G.} and Pugh, {David. S.} and Mark Reid and Taylor, {Richard J. K.}",
year = "2010",
month = mar,
doi = "10.1055/s-0029-1218521",
language = "English",
pages = "602--606",
journal = "Synlett",
issn = "1437-2096",
publisher = "Georg Thieme Verlag",
number = "4",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process

AU - Beltran-Rodil, Sandra

AU - Edwards, Michael G.

AU - Pugh, David. S.

AU - Reid, Mark

AU - Taylor, Richard J. K.

PY - 2010/3

Y1 - 2010/3

N2 - Two consecutive tandem processes are described for the regioselective, two-step synthesis of 1,3,5-trisubstituted pyrazoles from alpha-hydroxyketones. The first, a tandem MnO2-mediated oxidation/Ramirez olefination reaction, provides a facile route to beta,beta-dibromo-enones. These valuable 1,3-dicarbonyl synthons can then be converted into 1,3,5-trisubstituted pyrazoles via a second tandem hydrazine condensation/Suzuki-Miyaura cross-coupling reaction. Using these procedures, a range of aryl and alkyl alpha-hydroxyketones have been transformed regioselectively into 1,3,5-trisubstituted pyrazoles.

AB - Two consecutive tandem processes are described for the regioselective, two-step synthesis of 1,3,5-trisubstituted pyrazoles from alpha-hydroxyketones. The first, a tandem MnO2-mediated oxidation/Ramirez olefination reaction, provides a facile route to beta,beta-dibromo-enones. These valuable 1,3-dicarbonyl synthons can then be converted into 1,3,5-trisubstituted pyrazoles via a second tandem hydrazine condensation/Suzuki-Miyaura cross-coupling reaction. Using these procedures, a range of aryl and alkyl alpha-hydroxyketones have been transformed regioselectively into 1,3,5-trisubstituted pyrazoles.

KW - tandem oxidation process

KW - TOP

KW - beta,beta-dibromo-enones

KW - 1,3,5-trisubstituted pyrazoles

KW - Suzuki-Miyaura

KW - ONE-POT CONVERSION

KW - OXIDATION PROCESSES

KW - MANGANESE-DIOXIDE

KW - KETONES

KW - 1,1-DIBROMO-1-ALKENES

KW - DERIVATIVES

KW - ALKYNES

U2 - 10.1055/s-0029-1218521

DO - 10.1055/s-0029-1218521

M3 - Article

SP - 602

EP - 606

JO - Synlett

JF - Synlett

SN - 1437-2096

IS - 4

M1 - D27509ST

ER -