One-Pot Synthetic Routes to Multiply Substituted Indene Derivatives by Hydrolysis of Zirconocene-Mediated Intermolecular Coupling Reactions of Aromatic Ketones and Alkynes

2003 ◽  
Vol 68 (4) ◽  
pp. 1252-1257 ◽  
Author(s):  
Zhenfeng Xi ◽  
Ruiyun Guo ◽  
Shizue Mito ◽  
Hongliang Yan ◽  
Ken-ichiro Kanno ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
One Pot ◽  
Aromatic Ketones ◽  
Synthetic Routes ◽  
Hydrolysis Of ◽  
Intermolecular Coupling

Synthesis of Chlorinated Arenes and Hetarenes by One-Pot Cyclizations of 1,3-Bis-silyl Enol Ethers

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 665-673 ◽  
Author(s):  
Peter Langer ◽  
Zahid Hassan
Keyword(s):  
Cost Effective ◽  
Coupling Reactions ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Cross Coupling Reactions ◽  
Silyl Enol Ether ◽  
Synthetic Routes ◽  
Metal Catalyzed ◽  
High Level

This account describes our recent findings and progress in synthesizing chlorinated arenes and hetarenes by one-pot cyclizations of 1,3-bis-silyl enol ether derivatives. These reactions allow for the preparation of highly functionalized products with a high level of regioselectivity. The synthetic routes are cost-effective avoiding additional functionalization steps. The products are difficult to be accessed by other methods. The chlorine atom is of relevance in medicinal and agriculture chemistry. In addition, it allows further functionalizations by transition-metal-catalyzed cross-coupling reactions.1 Introduction2 Cyclizations of 2-Chloro-1,3-bis(silyloxy)-1,3-butadienes2.1 3,5-Dihydroxychlorophthalates2.2 2,4-Dihydroxy-homochlorophthalates2.3 2-(Arylsulfonyl)chloropyridines2.4 1-Azaxanthones3 Cyclizations of 4-Chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes3.1 3-Chlorosalicylates3.2 Functionalized Chlorobiaryls3.3 3-Chloro-5-(2-chloroethyl)-salicylates3.4 2,4-Dihydroxychlorobenzophenones4 Cyclizations of 2-Chloro-3-(silyloxy)-2-en-1-ones4.1 Functionalized Chlorophenols4.2 Functionalized Chlorinated Biaryls and Chlorofluorenones4.3 Functionalized Chlorochromenones4.4 Functionalized 3-(Methylthio)chlorophenols4.5 Functionalized 3-Chloromethylphenols5 Conclusions6 List of Abbreviations

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>

A Facile One-pot Synthesis of Substituted Quinolines via Cascade Friedlander Reaction from Isoxazoles with Ammonium Formate-Pd/C and Ketones

2020 ◽  
Vol 17 (3) ◽  
pp. 211-215
Author(s):  
Da Chen ◽  
Xuan Wang ◽  
Runnan Wang ◽  
Yao Zhan ◽  
Xiaohan Peng ◽  
...  
Keyword(s):  
Hydrogen Transfer ◽  
Ammonium Formate ◽  
Aromatic Ketone ◽  
Reaction Conditions ◽  
One Pot ◽  
Diverse Range ◽  
Strong Base ◽  
Aromatic Ketones ◽  
Substituted Quinolines ◽  
New Strategy

The Friedlander reaction is the most commonly used method to synthesis substituted quinolines, the essential intermediates in the medicine industry. A facile one-pot approach for synthesizing substituted quinolines by the reaction of isoxazoles, ammonium formate-Pd/C, concentrated sulfuric acid, methanol and ketones using Friedlander reaction conditions is reported. Procedures for the synthesis of quinoline derivatives were optimized, and the yield was up to 90.4%. The yield of aromatic ketones bearing electron-withdrawing groups was better than the ones with electron-donating substituents. The structures of eight substituted quinolines were characterized by MS, IR, H-NMR and 13CNMR, which were in agreement with the expected structures. The mechanism for the conversion was proposed, which involved the Pd/C catalytic hydrogen transfer reduction of unsaturated five-membered ring of isoxazole to produce ortho-amino aromatic ketones. Then the nucleophilic addition of with carbonyl of the ketones generated Schiff base in situ, which underwent an intermolecular aldol reaction followed by the elimination of H2O to give production of substituted quinolines. This new strategy can be readily applied for the construction of quinolines utilizing a diverse range of ketones and avoids the post-reaction separation of the o-amino aromatic ketone compounds. The conventionally used o-amino aromatic ketone compounds in Friedlander reaction to prepare substituted quinoline are laborious to synthesize and are apt to self-polymerize. While oxazole adopted in this work can be prepared at ease by the condensation of benzoacetonitrile and nitrobenzene derivatives under the catalysis of a strong base. Moreover, the key features of this protocol are readily available starting materials, excellent functional group tolerance, mild reaction conditions, operational simplicity, and feasibility for scaling up.

scholarly journals A One-Pot Approach to Novel Pyridazine C-Nucleosides

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2341
Author(s):  
Flavio Cermola ◽  
Serena Vella ◽  
Marina DellaGreca ◽  
Angela Tuzi ◽  
Maria Rosaria Iesce
Keyword(s):  
Organic Chemistry ◽  
Research Field ◽  
Modified Nucleosides ◽  
Protecting Groups ◽  
Coupling Reactions ◽  
One Pot ◽  
Pharmacological Interest ◽  
Classical Methodology ◽  
Glycosyl Donor ◽  
Neutral Conditions

The synthesis of glycosides and modified nucleosides represents a wide research field in organic chemistry. The classical methodology is based on coupling reactions between a glycosyl donor and an acceptor. An alternative strategy for new C-nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone. This approach is applied to obtain novel pyridazine C-nucleosides starting with 2- and 3-(ribofuranosyl)furans. It is based on singlet oxygen [4+2] cycloaddition followed by reduction and hydrazine cyclization under neutral conditions. The mild three-step one-pot procedure leads stereoselectively to novel pyridazine C-nucleosides of pharmacological interest. The use of acetyls as protecting groups provides an elegant direct route to a deprotected new pyridazine C-nucleoside.

scholarly journals 1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1214
Author(s):  
Sergey N. Podyachev ◽  
Rustem R. Zairov ◽  
Asiya R. Mustafina
Keyword(s):  
Structural Diversity ◽  
Building Blocks ◽  
Structural Features ◽  
Structure Property ◽  
One Pot ◽  
Arene Ligands ◽  
Structure Property Relationships ◽  
New Type ◽  
Synthetic Routes ◽  
Magnetic Resonance Imaging Mri

The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure–property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.

Rhenium- and Aniline-Catalyzed One-Pot Annulation of Aromatic Ketones and α,β-Unsaturated Esters Initiated by CH Bond Activation

2006 ◽  
Vol 118 (17) ◽  
pp. 2832-2834 ◽  
Author(s):  
Yoichiro Kuninobu ◽  
Yuta Nishina ◽  
Makoto Shouho ◽  
Kazuhiko Takai
Keyword(s):  
Bond Activation ◽  
One Pot ◽  
Aromatic Ketones ◽  
Unsaturated Esters
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