Formation of quaternary carbons through cobalt-catalyzed C(sp3)–C(sp3) Negishi cross-coupling

2020 ◽  
Vol 56 (59) ◽  
pp. 8210-8213 ◽  
Author(s):  
Eduardo Palao ◽  
Enol López ◽  
Iván Torres-Moya ◽  
Antonio de la Hoz ◽  
Ángel Díaz-Ortiz ◽  
...  
Keyword(s):  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Quaternary Carbons

Formation of all-carbon-substituted quaternary carbons is a key challenge in organic and medicinal chemistry.

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

scholarly journals Convenient Access to Functionalized Non-Symmetrical Atropisomeric 4,4′-Bipyridines

Compounds ◽  
2021 ◽  
Vol 1 (2) ◽  
pp. 58-74
Author(s):  
Emmanuel Aubert ◽  
Emmanuel Wenger ◽  
Paola Peluso ◽  
Victor Mamane
Keyword(s):  
Solid State ◽  
Intermolecular Interactions ◽  
Medicinal Chemistry ◽  
Crystal Packing ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Halogen Bonds ◽  
Cross Coupling Reactions ◽  
Cyano Groups ◽  
Post Functionalization

Non-symmetrical chiral 4,4′-bipyridines have recently found interest in organocatalysis and medicinal chemistry. In this regard, the development of efficient methods for their synthesis is highly desirable. Herein, a series of non-symmetrical atropisomeric polyhalogenated 4,4′-bipyridines were prepared and further functionalized by using cross-coupling reactions. The desymmetrization step is based on the N-oxidation of one of the two pyridine rings of the 4,4′-bipyridine skeleton. The main advantage of this methodology is the possible post-functionalization of the pyridine N-oxide, allowing selective introduction of chlorine, bromine or cyano groups in 2- and 2′-postions of the chiral atropisomeric 4,4′-bipyridines. The crystal packing in the solid state of some newly prepared derivatives was analyzed and revealed the importance of halogen bonds in intermolecular interactions.

scholarly journals Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross-Coupling To Generate Quaternary Carbons

2020 ◽  
Vol 142 (19) ◽  
pp. 8928-8937
Author(s):  
Jesús G. Estrada ◽  
Wendy L. Williams ◽  
Stephen I. Ting ◽  
Abigail G. Doyle
Keyword(s):  
Cross Coupling ◽  
Quaternary Carbons

Synthesis of Novel 2-diethylamino-4H-7-(Het) aryl pyrido[1,2-a][1,3,5]triazin-4-ones via a Suzuki Cross-Coupling Reaction of 2-Diethylamino-4H-7-iodopyrido[1,2a][1,3,5]triazin-4-one with (Het) arylboronic Acids in Water

2021 ◽  
Vol 12 (3) ◽  
pp. 563-572
Author(s):  
Said Dagdag ◽  
Mounir Belbahloul ◽  
Maria Kopp ◽  
Abdellah Anouar ◽  
Moustafa Chhiba ◽  
...  
Keyword(s):  
Medicinal Chemistry ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Biological Evaluation ◽  
One Pot ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction ◽  
Physico Chemical ◽  
Carbon Carbon Bonds ◽  
Carbon Molecules

Suzuki cross coupling reaction is one of the most famous organic reactions of the 20th century’s chemistry. It is deemed of as one of the most famous reaction in the field of chemistry. It is a very effective method for making carbon–carbon bonds. It has been extensively utilized in the synthesis of many carbon molecules including the most complex ones.Syntheses of 2-diethylamino-4H-7-(Het) aryl pyrido [1,2-a] [1,3,5] triazin-4-ones are currently under investigation in order to obtain great potentialities in medicinal chemistry of compounds class. The methodology we propose herein is able to produce numerous 2-diethylamino-4H-7-(Het)arylpyrido[1,2-a][1,3,5]triazin-4-one and derivatives that were synthesized, purified and characterized by 1HNMR, 13CNMR, MS techniques. Furthermore, it allows sequential introduction of various substituents into a 2-alkylylamino-4H-7-(Het)arylpyrido[1,2-a][1,3,5]triazin-4-ones ring using a one-pot procedure. The biological evaluation as well as the physico-chemical characterisation of various products are currently under way and will be described elsewhere.

ChemInform Abstract: Synthesis of Heteroaryl ortho-Phenoxyethylamines via Suzuki Cross-Coupling: Easy Access to New Potential Scaffolds in Medicinal Chemistry.

ChemInform ◽  
2016 ◽  
Vol 47 (16) ◽  
Author(s):  
Leda Ivanova Manasieva ◽  
Battisti Umberto Maria ◽  
Adolfo Prandi ◽  
Livio Brasili ◽  
Silvia Franchini
Keyword(s):  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Easy Access

scholarly journals Synthetic Strategies, Reactivity and Applications of 1,5-Naphthyridines

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3252
Author(s):  
Maria Fuertes ◽  
Carme Masdeu ◽  
Endika Martin-Encinas ◽  
Asier Selas ◽  
Gloria Rubiales ◽  
...  
Keyword(s):  
Metal Complexes ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
Cross Coupling ◽  
Side Chains ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Nucleophilic Reagents

This review covers the synthesis and reactivity of 1,5-naphthyridine derivatives published in the last 18 years. These heterocycles present a significant importance in the field of medicinal chemistry because many of them exhibit a great variety of biological activities. First, the published strategies related to the synthesis of 1,5-naphthyridines are presented followed by the reactivity of these compounds with electrophilic or nucleophilic reagents, in oxidations, reductions, cross-coupling reactions, modification of side chains or formation of metal complexes. Finally, some properties and applications of these heterocycles studied during this period are examined.

scholarly journals Synthesis of New 2-Arylbenzo[b]furan Derivatives via Palladium-Catalyzed Suzuki Cross-Coupling Reactions in Aqueous Media

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2450 ◽  
Author(s):  
Qianqian Chen ◽  
Panli Jiang ◽  
Mengping Guo ◽  
Jianxin Yang
Keyword(s):  
Medicinal Chemistry ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Furan Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

A series of novel benzofuran derivatives containing biaryl moiety were designed and synthesized by the Suzuki cross-coupling reactions. The reactions, performed in the presence of K2CO3, EtOH/H2O and Pd(II) complex as catalyst, gave the corresponding products in good to excellent yields. The methodology allows the facile production of heterobiaryl compounds, a unique architectural motif that is ubiquitous in medicinal chemistry.

Synthesis of phenylacetic acid regioisomers possessing an N-substituted 1,2-dihydropyrid-2-one pharmacophore — Evaluation as inhibitors of cyclooxygenases and 5-lipoxygenase

2011 ◽  
Vol 89 (6) ◽  
pp. 617-622 ◽  
Author(s):  
Gang Yu ◽  
Morshed A. Chowdhury ◽  
Zhangjian Huang ◽  
Khaled R. A. Abdellatif ◽  
Edward E. Knaus
Keyword(s):  
Medicinal Chemistry ◽  
Phenylacetic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ring System ◽  
Ring Systems ◽  
Cross Coupling Reaction

The Suzuki–Miyaura cross-coupling reaction provides a useful method for the synthesis of methyl 2-(2-chloropyridyl or 2-methoxypyridyl)phenylacetates. The 2-chloropyridyl or 2-methoxypyridyl ring system can be readily elaborated to N-substituted (OH, Me, CHF2, H) 1,2-dihydropyrid-2-one ring systems that are useful synthons for use in bioorganic and medicinal chemistry applications.

scholarly journals Profiling and Application of Photoredox C(sp3)–C(sp2) Cross-Coupling in Medicinal Chemistry

2018 ◽  
Vol 9 (7) ◽  
pp. 773-777 ◽  
Author(s):  
Rui Zhang ◽  
Guoqing Li ◽  
Michael Wismer ◽  
Petr Vachal ◽  
Steven L. Colletti ◽  
...  
Keyword(s):  
Medicinal Chemistry ◽  
Cross Coupling

scholarly journals Decarboxylative cross-coupling reactions for P(O)–C bond formation

RSC Advances ◽  
2018 ◽  
Vol 8 (46) ◽  
pp. 26383-26398 ◽  
Author(s):  
Akram Hosseinian ◽  
Fatemeh Alsadat Hosseini Nasab ◽  
Sheida Ahmadi ◽  
Zahra Rahmani ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Organic Compounds ◽  
Medicinal Chemistry ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Materials Chemistry ◽  
Cross Coupling Reactions ◽  
Agricultural Chemistry ◽  
Phosphorus Containing

Phosphorus-containing compounds are one of the most important classes of organic compounds, which have wide applications in organic chemistry, medicinal chemistry, agricultural chemistry, and materials chemistry.

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