scholarly journals A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

2014 ◽  
Vol 10 ◽  
pp. 722-731
Author(s):  
Natalia V Pavlenko ◽  
Tatiana I Oos ◽  
Yurii L Yagupolskii ◽  
Igor I Gerus ◽  
Uwe Doeller ◽  
...  
Keyword(s):  
Amino Acids ◽  
Ethyl Ester ◽  
Nucleophilic Addition ◽  
Phosphinic Acid ◽  
Double Bonds ◽  
Synthetic Methodology ◽  
One Pot ◽  
Phosphinic Acids

A series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of proteinogenic and nonproteinogenic α-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds.

A Convenient One-Pot Preparation of Disubstituted Phosphinic Acids Derived from Simple Amino Acids and Proline

Synthesis ◽  
1995 ◽  
Vol 1995 (09) ◽  
pp. 1074-1076 ◽  
Author(s):  
Marianne Borloo ◽  
Xian-Yun Jiao ◽  
Halina Wójtowicz ◽  
Padinchare Rajan ◽  
Christophe Verbruggen ◽  
...  
Keyword(s):  
Amino Acids ◽  
One Pot ◽  
Phosphinic Acids

ChemInform Abstract: A Convenient One-Pot Preparation of Disubstituted Phosphinic Acids Derived from Simple Amino Acids and Proline.

ChemInform ◽  
2010 ◽  
Vol 27 (2) ◽  
pp. no-no
Author(s):  
M. BORLOO ◽  
X.-Y. JIAO ◽  
H. WOJTOWICZ ◽  
P. RAJAN ◽  
C. VERBRUGGEN ◽  
...  
Keyword(s):  
Amino Acids ◽  
One Pot ◽  
Phosphinic Acids

scholarly journals Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

2011 ◽  
Vol 7 ◽  
pp. 1570-1576 ◽  
Author(s):  
Elizabeth P Jones ◽  
Peter Jones ◽  
Andrew J P White ◽  
Anthony G M Barrett
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Coupling Reaction ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Aryl Group ◽  
Hydrolysis Of

A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

scholarly journals A Water-Soluble Copper-Immobilized Covalent Organic Framework Functioning as an “OFF–ON” Fluorescent Sensor for Amino Acids

2021 ◽  
Author(s):  
Lamiaa Reda Ahmed ◽  
Ahmed F. M. EL-Mahdy ◽  
Cheng-Tang Pan ◽  
Shiao-Wei Kuo
Keyword(s):  
Amino Acids ◽  
Fluorescent Sensor ◽  
Water Soluble ◽  
One Pot ◽  
Covalent Organic Framework ◽  
The One ◽  
Organic Framework

In this paper, we describe the construction of a new fluorescent hydroxyl- and hydrazone-based covalent organic framework (TFPB-DHTH COF) through the one-pot polycondensation of 1,3,5-tris(4-formylphenyl)benzene (TFPB) and 2,5-dihydroxyterephthalohydrazide (DHTH) under...

A facile one pot route for the synthesis of imide tethered peptidomimetics

2016 ◽  
Vol 14 (2) ◽  
pp. 556-563 ◽  
Author(s):  
Veladi Panduranga ◽  
Girish Prabhu ◽  
Roopesh Kumar ◽  
Basavaprabhu Basavaprabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
One Pot ◽  
Protected Amino Acid

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

The 4-(methylthio)phenyl ester for the synthesis of polypeptides of a known repeating sequence of amino acids. Synthesis of poly-(L-lysylglycyl)glycine 1-C14 ethyl ester hydrobromide

1970 ◽  
Vol 48 (16) ◽  
pp. 2509-2511 ◽  
Author(s):  
Brian J. Johnson ◽  
Donna S. Rea
Keyword(s):  
Amino Acids ◽  
Ethyl Ester ◽  
Title Compound ◽  
Ester Hydrochloride ◽  
Phenyl Ester ◽  
Protecting Group ◽  
High Dilution ◽  
Protective Groups ◽  
Protected Tetrapeptide

The synthesis of the tetrapeptide, N-t-butoxycarbonyl-ε-N-carbobenzoxy-L-lysylglycyl-ε-N-carbobenzoxy-L-lysylglycine 4-(methylthio)phenyl ester is described. The utility of this protective ester is shown by its easy conversion to the protected tetrapeptide 4-(methylsulfonyl)phenyl activated ester without decomposition. Removal of the N-butoxycarbonyl protecting group afforded the polymerizing unit, ε-N-carbobenzoxy-L-lysylglycyl-ε-N-carbobenzoxy-L-lysylglycine 4-(methylsulfonyl)phenyl ester. Polymerization of this material on the partially blocked monomer glycine-1-C14 ethyl ester hydrochloride, at a relatively high dilution, gave poly-(ε-N-carbobenzoxyl-L-lysylglycyl)glycine-1-C14 ethyl ester. The carbobenzoxy protective groups were removed to give the title compound.

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