Synthetic studies of novel ninhydrin analogs

2001 ◽  
Vol 79 (11) ◽  
pp. 1632-1654 ◽  
Author(s):  
Richard R Hark ◽  
Diane B Hauze ◽  
Olga Petrovskaia ◽  
Madeleine M Joullié
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Latent Fingerprints ◽  
Cross Coupling Reactions ◽  
Essential Tool ◽  
Porous Surfaces ◽  
Synthetic Studies ◽  
Sulfur Containing

Ninhydrin is an essential tool in the analysis of amino acids, peptides, and proteins, and the preferred reagent for the detection of latent fingerprints on porous surfaces. The goal of this investigation was to prepare ninhydrin analogs with enhanced chromogenic and fluorogenic properties. Target compounds included structures with extended conjugation and (or) with the presence of sulfur-containing moieties. We have devised general convergent routes for novel heterocyclic and aryl-substituted ninhydrin analogs for use as reagents for amino acid detection.Key words: ninhydrin analogs, synthesis, ketals, Suzuki cross-coupling reactions, Stille cross-coupling reactions.

scholarly journals Synthesis of C 3-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step

2019 ◽  
Vol 15 ◽  
pp. 371-377 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Saidulu Todeti
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Negishi Coupling ◽  
Peptide Dendrimers ◽  
Cross Coupling Reactions ◽  
Synthetic Strategy ◽  
Symmetric Star ◽  
Key Steps

We demonstrate a new synthetic strategy toward star-shaped C 3-symmetric molecules containing α-amino acid (AAA) derivatives and dipeptides. In this regard, trimerization and Negishi cross-coupling reactions are used as the key steps starting from readily available 4’-iodoacetophenone and L-serine. These C 3-symmetric molecules containing AAA moieties are useful to design new ligands suitable for asymmetric synthesis and peptide dendrimers.

SUZUKI CROSS-COUPLING REACTIONS OF NONRACEMIC VINYLBORONO-α-AMINO ACIDS

2001 ◽  
Vol 31 (2) ◽  
pp. 249-255 ◽  
Author(s):  
Sylvain Collet ◽  
Renée Danion-Bougot ◽  
Daniel Danion
Keyword(s):  
Amino Acids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions

2019 ◽  
Vol 84 (5) ◽  
pp. 3004-3010 ◽  
Author(s):  
Gargi Nikhil Vaidya ◽  
Arif Khan ◽  
Hansa Verma ◽  
Sanjeev Kumar ◽  
Dinesh Kumar
Keyword(s):  
Amino Acids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Relationship Of

Visible-light-induced iodine anion catalyzed decarboxylative/ deaminative C-H alkylation of enamides

2021 ◽  
Author(s):  
Jia-Xin Wang ◽  
Ya-Ting Wang ◽  
Hao Zhang ◽  
Ming-Chen Fu
Keyword(s):  
Amino Acid ◽  
Visible Light ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Active Esters ◽  
Cross Coupling Reactions ◽  
Redox Active ◽  
Iodine Anion

A visible-light-induced iodine anion catalyzed C-H stereoselective alkylation of enamides has been developed. Redox-active esters and Katritzky salts of the amino acid are amenable for decarboxylative/deaminative cross-coupling reactions, delivering various...

scholarly journals Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

2012 ◽  
Vol 8 ◽  
pp. 2004-2018 ◽  
Author(s):  
Rajendra Surasani ◽  
Dipak Kalita ◽  
A V Dhanunjaya Rao ◽  
K B Chandrasekhar
Keyword(s):  
Amino Acid ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Acid Esters ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Acid Esters

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

ChemInform Abstract: Negishi Cross-Coupling Reactions of α-Amino Acid-Derived Organozinc Reagents and Aromatic Bromides.

ChemInform ◽  
2008 ◽  
Vol 39 (24) ◽  
Author(s):  
Claire L. Oswald ◽  
Tomas Carrillo-Marquez ◽  
Lorenzo Caggiano ◽  
Richard F. W. Jackson
Keyword(s):  
Amino Acid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Organozinc Reagents
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