scholarly journals α-(Imino)pyridyldifluoroethyl Phosphonates: Novel Promising Building Blocks in Synthesis of Biorelevant Aminophosphonic Acids Derivatives

Organics ◽  
2021 ◽  
Vol 2 (2) ◽  
pp. 72-83
Author(s):  
Oksana M. Shavrina ◽  
Lyudmyla V. Bezgubenko ◽  
Andrii V. Bezdudny ◽  
Petro P. Onys’ko ◽  
Yuliya V. Rassukana
Keyword(s):  
Carbon Atom ◽  
Building Blocks ◽  
Synthetic Approach ◽  
Phosphonic Acids ◽  
Aminophosphonic Acids ◽  
Convenient Synthetic Approach

A convenient synthetic approach to previously unknown NH-iminophosphonates bearing 2-, 3-, and 4-pyridyldifluoromethyl groups at the imine carbon atom was developed. The synthetic potential of these novel building blocks was demonstrated by their conversion into highly functionalized acyclic and heterocyclic aminophosphonates and phosphonic acids combining in their structure biorelevant aminophosphonic fragment, difluoromethyl group, and pyridyl, piperidyl, thiazolidin-4-one, or thiazidinan-4-one heterocyclic moieties in a single molecular platform.

scholarly journals The preparative synthetic approach to 4-(trifluoromethoxy)piperidine and 4-(trifluoromethoxymethyl)piperidine

2021 ◽  
Vol 19 (1(73)) ◽  
pp. 3-9
Author(s):  
Ivan G. Logvinenko ◽  
Violetta G. Dolovanyuk ◽  
Ivan S. Kondratov
Keyword(s):  
Mass Spectrometry ◽  
Benzoyl Chloride ◽  
Building Blocks ◽  
Secondary Amines ◽  
Synthetic Approach ◽  
Synthetic Strategy ◽  
Benzoyl Group ◽  
Two Stages ◽  
13C And 19F Nmr ◽  
Convenient Synthetic Approach

Aim. To develop a convenient synthetic approach for the preparation of multigram amounts of 4-(trifluoromethoxy)-piperidine and 4-(trifluoromethoxymethyl)piperidine – promising building blocks for medicinal chemistry.Results and discussion. 4-(Trifluoromethoxy)piperidine (8.4 g) and 4-(trifluoromethoxymethyl)piperidine (12.9 g) were synthesized in 5 stages starting from 4-hydroxypiperidine (the overall yield 40 %) and 4-(hydroxymethyl)piperidine (the overall yield 13.5 %), respectively.Experimental part. The first stage of the synthetic strategy was acylation of 4-hydroxypiperidine with benzoyl chloride. N-benzoyl-4-hydroxypiperidine obtained was transformed to N-benzoyl-4-(trifluoromethoxy)piperidine in two stages using the Hiyama method (the synthesis of the corresponding S-methyl xanthate with the subsequent desulfurization/fluorination using N-bromosuccinimide and Olah’s reagent). Then the N-benzoyl group was reduced to benzyl one, which was removed using 1-chloroethyl chloroformate. The similar approach was applied to the synthesis of 4-(trifluoromethoxymethyl)piperidine starting from 4-(hydroxymethyl)piperidine. The structure and composition of the compounds synthesized were confrmed by 1Н, 13C and 19F NMR spectroscopy,mass-spectrometry and elemental analysis.Conclusions. The synthetic approach developed is a convenient method for the multigram preparation of4-(trifluoromethoxy)piperidine and 4-(trifluoromethoxymethyl)piperidine and can be used for the synthesis of other secondary amines containing the CF3O-group.Key words: fluorination; trifluoromethoxy group; xanthate; piperidine; protection group

scholarly journals A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

Organics ◽  
2021 ◽  
Vol 2 (2) ◽  
pp. 107-117
Author(s):  
Mattia Forchetta ◽  
Valeria Conte ◽  
Giulia Fiorani ◽  
Pierluca Galloni ◽  
Federica Sabuzi
Keyword(s):  
Metal Oxides ◽  
Phosphonic Acid ◽  
Organic Molecules ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Phosphonic Acids ◽  
Sustainable Improvement ◽  
Phosphonate Esters ◽  
First Time ◽  
Complex Organic

Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

Convenient synthetic approach towards high alcohol esters of 5-aryl-2,2′-bipyridine-5′-carboxylic acids

2020 ◽  
Author(s):  
Dmitry S. Kopchuk ◽  
Ekaterina S. Starnovskaya ◽  
Yaroslav K. Shtaitz ◽  
Maria I. Savchuk ◽  
Alexey P. Krinochkin ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Synthetic Approach ◽  
High Alcohol ◽  
Convenient Synthetic Approach

Convenient Synthetic Approach to 2,4-Disubstituted Quinazolines

2007 ◽  
Vol 9 (1) ◽  
pp. 69-72 ◽  
Author(s):  
Serena Ferrini ◽  
Fabio Ponticelli ◽  
Maurizio Taddei
Keyword(s):  
Synthetic Approach ◽  
Convenient Synthetic Approach

scholarly journals Convenient Synthetic Approach to 2,4-Disubstituted Quinazolines.

ChemInform ◽  
2007 ◽  
Vol 38 (20) ◽  
Author(s):  
Serena Ferrini ◽  
Fabio Ponticelli ◽  
Maurizio Taddei
Keyword(s):  
Synthetic Approach ◽  
Convenient Synthetic Approach

scholarly journals Flat Crown Ethers with Planar Tetracoordinate Carbon Atoms

2020 ◽  
Author(s):  
Venkatesan Thimmakondu ◽  
Krishnan Thirumoorthy
Keyword(s):  
Carbon Atom ◽  
Crown Ether ◽  
Crown Ethers ◽  
In Silico ◽  
Alkaline Earth ◽  
Experimental Studies ◽  
Building Blocks ◽  
Binding Energies ◽  
High Symmetry ◽  
Structural Rigidity

Novel flat crown ether molecules have been characterized in silico using DFT hybrid and hybrid-meta functionals. Monomer units of Si2C3 with a planar tetracoordinate carbon atom have been used as building blocks. Alkali (Li+, Na+, K+, Rb+, and Cs+) and alkaline-earth (Ca2+, Sr2+, and Ba2+) metals, and uranyl (UO2+ 2 ) ion selective complexes have also been theoretically identified. The high symmetry and higher structural rigidity of the host molecules may likely to impart higher selectivity in chelation. Theoretical binding energies have been computed and experimental studies are invited.

scholarly journals A Straightforward Methodology to Overcome Solubility Challenges for N-Terminal Cysteinyl Peptide Segments Used in Native Chemical Ligation

2020 ◽  
Author(s):  
Skander Abboud ◽  
El hadji Cisse ◽  
Michel Doudeau ◽  
Hélène Bénédetti ◽  
Vincent AUCAGNE
Keyword(s):  
Amino Acids ◽  
Chemical Synthesis ◽  
Building Blocks ◽  
Native Chemical Ligation ◽  
Synthetic Approach ◽  
Chemical Ligation ◽  
Limited Solubility ◽  
Peptide Segments

One of the main limitations encountered during the chemical synthesis of proteins through native chemical ligation (NCL) is the limited solubility of some of the peptide segments. The most commonly used solution to overcome this problem is to derivatize the segment with a temporary solubilizing tag. Conveniently, the tag can be introduced on the thioester segment in such a way that it is removed concomitantly with the NCL reaction. We herein describe a generalization of this approach to N-terminal cysteinyl segment counterparts, using a straightforward synthetic approach that can be easily automated from commercially available building blocks, and applied it to a well-known problematic target, SUMO-2 (93 amino acids).

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