scholarly journals Synthesis of Functionalized Cannabilactones

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 684
Author(s):  
Yingpeng Liu ◽  
Thanh C. Ho ◽  
Mohammed Baradwan ◽  
Maria Pascual Lopez-Alberca ◽  
Christos Iliopoulos-Tsoutsouvas ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
New Approach ◽  
Structural Modifications ◽  
Cross Coupling Reaction ◽  
One Step

A new approach to synthesize cannabilactones using Suzuki cross-coupling reaction followed by one-step demethylation-cyclization is presented. The two key cannabilactone prototypes AM1710 and AM1714 were obtained selectively in high overall yields and in a lesser number of synthetic steps when compared to our earlier synthesis. The new approach expedited the synthesis of cannabilactone analogs with structural modifications at the four potential pharmacophoric regions.

scholarly journals A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

2019 ◽  
Vol 15 ◽  
pp. 2569-2576 ◽  
Author(s):  
Thines Kanagasundaram ◽  
Antje Timmermann ◽  
Carsten S Kramer ◽  
Klaus Kopka
Keyword(s):  
Free Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Stimulated Emission ◽  
New Approach ◽  
Cross Coupling Reaction ◽  
Optimal Coupling ◽  
Sensor Molecules ◽  
Optimized Conditions ◽  
Coupling Partner

Background: Silicon rhodamines are of particular interest because of their advantageous dye properties (fluorescence- and biostability, quantum efficiency, tolerance to photobleaching). Therefore, silicon rhodamines find frequent application in STED (stimulated emission depletion) microscopy, as sensor molecules for, e.g., ions and as fluorophores for the optical imaging of tumors. Different strategies were already employed for their synthesis. Because of just three known literature examples in which Suzuki–Miyaura cross couplings gave access to silicon rhodamines in poor to moderate yields, we wanted to improve these first valuable experimental results. Results: The preparation of the xanthene triflate was enhanced and several boron sources were screened to find the optimal coupling partner. After optimization of the palladium catalyst, different substituted boroxines were assessed to explore the scope of the Pd-catalyzed cross-coupling reaction. Conclusions: A number of silicon rhodamines were synthesized under the optimized conditions in up to 91% yield without the necessity of HPLC purification. Moreover, silicon rhodamines functionalized with free acid moieties are directly accessible in contrast to previously described methods.

scholarly journals One step synthesis of Diflunisal using a Pd-diamine complex

2009 ◽  
Vol 7 (4) ◽  
pp. 818-826 ◽  
Author(s):  
Tuula Kylmälä ◽  
Jan Tois ◽  
Youjun Xu ◽  
Robert Franzén
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
One Step ◽  
The One

AbstractDiflunisal and Felbinac, two FDA-approved NSAIDs and other biphenyl carboxylic acids were prepared in one step by a simple and clean Suzuki cross-coupling reaction using an easily synthesized, air and moisture stable, palladium-diamine complex. The yield (93%) for the one-step preparation of Diflunisal is the best reported without using a glovebox and a phoshine-based catalyst.

A new approach to access difluoroalkylated diarylmethanes via visible-light photocatalytic cross-coupling reactions

2018 ◽  
Vol 54 (32) ◽  
pp. 3993-3996 ◽  
Author(s):  
Yin-Na Zhao ◽  
Yong-Chun Luo ◽  
Zhu-Yin Wang ◽  
Peng-Fei Xu
Keyword(s):  
Visible Light ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Quinone Methide ◽  
Coupling Reactions ◽  
New Approach ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Visible Light Photocatalytic

A para-quinone methide and difluoroalkylating reagent involved radical cross-coupling reaction was described, through photocatalytically generated diarylmethane radical intermediates.

scholarly journals Synthesis of 3-Alkyl-6-Methyl-1,2,4,5-Tetrazines via a Sonogashira-Type Cross-Coupling Reaction

2020 ◽  
Author(s):  
Dominique Forson ◽  
Xavier Verdaguer ◽  
Lluís Ribas de Pouplana ◽  
Antoni Riera ◽  
Enric Ros ◽  
...  
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Chemical Biology ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
New Approach ◽  
Cross Coupling Reaction ◽  
Efficient Route

1,2,4,5-Tetrazines have become extremely useful tools in chemical biology. However, the synthesis of some challenging substrates such as 3,6-dialkyl-1,2,4,5-tetrazines is still a limitation for the widespread use of this class of compounds. Herein we describe an efficient route to these compounds based on the Sonogashira coupling of 3-bromo-6-methyl-1,2,4,5-tetrazine with terminal alkynes. The preparation of the starting reagent has been also optimized. The alkynyl products have been used as intermediates for the synthesis of dialkyl-tetrazines through a sequence of hydrogenation and re-oxidation with unprecedented yields. The synthetic applicability of this new approach is showcased through the preparation of several unnatural amino acids bearing alkynyl- and alkyl-1,2,4,5-tetrazine fragments.

scholarly journals Synthesis of 3-Alkyl-6-Methyl-1,2,4,5-Tetrazines via a Sonogashira-Type Cross-Coupling Reaction

2020 ◽  
Author(s):  
Dominique Forson ◽  
Xavier Verdaguer ◽  
Lluís Ribas de Pouplana ◽  
Antoni Riera ◽  
Enric Ros ◽  
...  
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Chemical Biology ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
New Approach ◽  
Cross Coupling Reaction ◽  
Efficient Route

1,2,4,5-Tetrazines have become extremely useful tools in chemical biology. However, the synthesis of some challenging substrates such as 3,6-dialkyl-1,2,4,5-tetrazines is still a limitation for the widespread use of this class of compounds. Herein we describe an efficient route to these compounds based on the Sonogashira coupling of 3-bromo-6-methyl-1,2,4,5-tetrazine with terminal alkynes. The preparation of the starting reagent has been also optimized. The alkynyl products have been used as intermediates for the synthesis of dialkyl-tetrazines through a sequence of hydrogenation and re-oxidation with unprecedented yields. The synthetic applicability of this new approach is showcased through the preparation of several unnatural amino acids bearing alkynyl- and alkyl-1,2,4,5-tetrazine fragments.

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