Regioselective C6‐Arylation of Thieno[3,2‐<i>c</i>]pyrazole Heterocycles with Aryl Iodides-Reference-Cited by-同舟云学术

Regioselective C6‐Arylation of Thieno[3,2‐c]pyrazole Heterocycles with Aryl Iodides

Published:2024-05-23 Issue:12 Volume:366 Page:2749-2757
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Ait Lfakir Noura¹²³,Jismy Badr¹,Guillaumet Gérald²⁴,Akssira Mohamed³,El Hakmaoui Ahmed³,Guillot Régis⁵,Tikad Abdellatif⁶,Abarbri Mohamed¹^ORCID

Affiliation:

1. Laboratoire de Physico-Chimie des Matériaux et des Electrolytes pour l'Energie (PCM2E) EA 6299 Faculté des Sciences et Techniques Université de Tours. Avenue Monge Faculté des Sciences, Parc de Grandmont 37200 Tours France

2. Institut de Chimie Organique et Analytique (ICOA) Université d'Orléans, UMR CNRS 7311 BP 6759 Rue de Chartres 45067 Orléans Cedex 2 France

3. Laboratoire de Chimie Physique et Biotechnologies des Biomolécules et des Matériaux, URAC 22. Faculté des Sciences et Techniques de Mohammedia Université Hassan II de Casablanca. B.P. 146 28800 Mohammedia Morocco

4. Euromed Research Center Euromed Faculty of Pharmacy Euromed University of Fes (UEMF) Meknes road Fes 30000 Morocco

5. Institut de Chimie Moléculaire et des Matériaux d'Orsay CNRS UMR 8182/ Université Paris-Saclay Bâtiment 670 Henri Moissan 1, 17, Avenue des Sciences 91400 Orsay France

6. Laboratoire de Chimie Moléculaire et Substances Naturelles. Université Moulay Ismail Faculté des Sciences B.P. 11201 Zitoune, Meknès Morocco

Abstract

AbstractRegioselective C6‐arylation of thieno[3,2‐c]pyrazoles with aryl iodides as coupling partners has been developed. This strategy was performed in the presence of Pd(OAc)2 as catalyst in combination with AgOTf as an oxidant and TFA in dimethylacetamide. In all experiments, only the C6‐arylated thieno[3,2‐c]pyrazole was isolated since its C5‐regioisomer was not observed, indicating the high regioselectivity of this approach. The catalytic system used is compatible with a variety of 3‐functionalized thieno[3,2‐c]pyrazoles and iodoaryl electrophiles, providing access to 3,6‐disubstituted thieno[3,2‐c]pyrazoles in yields ranging from 49% to 94%.

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202400141

Reference80 articles.

1. H. Inoue H. Murafuji Y. Hayashi Patent US7932250B2 2011.

2. R. Silverman P. Torrence B. K. Jha P. Francom Patent WO2007127212A2 2007.

3. A convenient synthesis and biological activity of novel thieno[2,3-c]pyrazole compounds as antimicrobial and anti-inflammatory agents

4. ASB16165, a phosphodiesterase 7A inhibitor, reduces cutaneous TNF-α level and ameliorates skin edema in phorbol ester 12-O-tetradecanoylphorbol-13-acetate-induced skin inflammation model in mice

5. The biological activity of new thieno[2,3-c]pyrazole compounds as anti-oxidants against toxicity of 4-nonylphenol in Clarias gariepinus