Tandem One-Pot Diels-Alder/Cross-Coupling Reactions of Organoindium Reagents

Synfacts ◽  
2010 ◽  
Vol 2010 (04) ◽  
pp. 0463-0463
Keyword(s):  
Cross Coupling ◽  
Diels Alder ◽  
Coupling Reactions ◽  
One Pot ◽  
Cross Coupling Reactions

Optimized Synthesis of 7-Aza-Indazoles by Diels–Alder Cascade and Associated Process Safety

2020 ◽  
Author(s):  
Nicolas Brach ◽  
Vincent Le Fouler ◽  
Vincent Bizet ◽  
Marian Lanz ◽  
Pascale Hoehn ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Process Safety ◽  
One Pot ◽  
Carbon And Nitrogen ◽  
Dsc Studies ◽  
Cross Coupling Reactions ◽  
Selection Of

Although pyrimidines are not among the most reac-tive partners in intramolecular inverse-electron de-mand [4πs+2πs] reactions with alkynes, they could be activated under mild and practical conditions, leading to fused nitrogen-containing heterocycles. We report an optimized synthesis of a 5-iodo-7-aza-indazole by a one-pot Diels–Alder cascade that starts from a pyrimidine substituted in the 2-position by an (alkynyl)hydrazone. The safety of the process was carefully studied by DSC studies. Eventually, a selection of cross-coupling reactions of 17 was studied and allowed the introduction of carbon- and nitrogen-based nucleophiles at the C5-position in good to excellent yields.

Optimized Synthesis of 7-Aza-Indazoles by Diels–Alder Cascade and Associated Process Safety

2020 ◽  
Author(s):  
Nicolas Brach ◽  
Vincent Le Fouler ◽  
Vincent Bizet ◽  
Marian Lanz ◽  
Pascale Hoehn ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Process Safety ◽  
One Pot ◽  
Carbon And Nitrogen ◽  
Dsc Studies ◽  
Cross Coupling Reactions ◽  
Selection Of

Although pyrimidines are not among the most reac-tive partners in intramolecular inverse-electron de-mand [4πs+2πs] reactions with alkynes, they could be activated under mild and practical conditions, leading to fused nitrogen-containing heterocycles. We report an optimized synthesis of a 5-iodo-7-aza-indazole by a one-pot Diels–Alder cascade that starts from a pyrimidine substituted in the 2-position by an (alkynyl)hydrazone. The safety of the process was carefully studied by DSC studies. Eventually, a selection of cross-coupling reactions of 17 was studied and allowed the introduction of carbon- and nitrogen-based nucleophiles at the C5-position in good to excellent yields.

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 Synthesis of pentasubstituted 2-aryl pyrroles from boryl and stannyl alkynes via one-pot sequential Ti-catalyzed [2 + 2 + 1] pyrrole synthesis/cross coupling reactions

2020 ◽  
Vol 11 (37) ◽  
pp. 10236-10242
Author(s):  
Yukun Cheng ◽  
Channing K. Klein ◽  
Ian A. Tonks
Keyword(s):  
Small Molecule ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Cross Coupling Reactions

Multisubstituted pyrroles are commonly found in many bioactive small molecule scaffolds, yet the synthesis of highly-substituted pyrrole cores remains challenging.

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