189341-90-0

Upstream product

• 98-98-6 2-Picolinic acid 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 67-56-1 methanol 
• 63-91-2 L-phenylalanine 
• 29745-44-6 pyridine-2-carbonyl chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 125470-94-2 3-phenyl-2-[(pyridine-2-carbonyl)amino]propionic acid 
• 1332650-41-5 methyl (S)-3-phenyl-2-(pyridine-2-carbothioamido)propanoate 
• 1332650-42-6 methyl (S)-2-(3-benzyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-yl)-3-phenylpropanoate 
• 1609203-99-7 (S)-methyl 2-(picolinamido)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 

Relevant academic research and scientific papers

Cobalt-Catalyzed C(sp2)-H Carbonylation of Amino Acids Using Picolinamide as a Traceless Directing Group

Herein we report an efficient protocol for the C(sp2)-H carbonylation of amino acid derivatives based on an inexpensive cobalt(II) salt catalyst. Carbonylation was accomplished using picolinamide as a traceless directing group, CO (1 atm) as the carbonyl

Synthesis of unnatural α-amino acid derivatives: Via selective o -C-H functionalization

Pd-Catalyzed o-C-H functionalization of α-phenylglycine, 4-hydroxyphenylglycine and phenylalanine using picolinamide as a directing group is reported. We have developed different protocols for the arylation, alkylation, alkynylation, halogenation, alkoxylation, and acyloxylation of these amino acids. The reactions exhibit high selectivity, broad substrate scope, and compatibility with different functional groups in moderate to high yields. They provide a rapid and efficient access to a variety of phenyl based amino acid derivatives which can be further modified and have broad spectrum of applications in medicinal chemistry.

Direct borylation of primary C-H bonds in functionalized molecules by palladium catalysis

Organoborane compounds are among the most commonly employed intermediates in organic synthesis and serve as crucial precursors to alcohols, amines, and various functionalized molecules. A simple palladium-based system catalyzes the conversion of primary C(sp3)-H bonds in functionalized complex organic molecules into alkyl boronate esters. Amino acids, amino alcohols, alkyl amines, and a series of bioactive molecules can be functionalized with the use of readily available and removable directing groups in the presence of commercially available additives, simple ligands, and oxygen (O2) as the terminal oxidant. This approach represents an economic and environmentally friendly method that could find broad applications. Crucial additives: A simple palladium-based system catalyzes the conversion of primary C(sp3)-H bonds in complex organic molecules into alkyl boronate esters. Amino acids, amino alcohols, alkyl amines, and a series of bioactive molecules that are modified with readily available directing groups are functionalized in the presence of commercially available additives, simple ligands, and oxygen as the terminal oxidant.

A convenient and efficient synthesis of dipeptidyl benzoxaboroles and their peptidomimetics

We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl) phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3- phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules. Georg Thieme Verlag Stuttgart ? New York.

Highly efficient syntheses of azetidines, pyrrolidines, and indolines via palladium catalyzed intramolecular amination of C(sp3)-H and C(sp2)-H bonds at γ and δ positions

Efficient methods have been developed to synthesize azetidine, pyrrolidine, and indoline compounds via palladium-catalyzed intramolecular amination of C-H bonds at the γ and δ positions of picolinamide (PA) protected amine substrates. These methods feature relatively a low catalyst loading, use of inexpensive reagents, and convenient operating conditions. Their selectivities are predictable. These methods highlight the use of unactivated C-H bond, especially the C(sp3)-H bond of methyl groups, as functional groups in organic synthesis.

Improved protocol for indoline synthesis via palladium-catalyzed intramolecular C(sp2)-H amination

An efficient method has been developed for the synthesis of indoline compounds from picolinamide (PA)-protected β-arylethylamine substrates via palladium-catalyzed intramolecular amination of ortho-C(sp2)-H bonds. These reactions feature high efficiency, low catalyst loadings, mild operating conditions, and the use of inexpensive reagents.

Efficient alkyl ether synthesis via palladium-catalyzed, picolinamide-directed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds at remote positions

We report the efficient synthesis of alkyl ethers by the functionalization of unactivated sp3- and sp2-hybridized C-H bonds. In the Pd(OAc)2-catalyzed, PhI(OAc)2-mediated reaction system, picolinamide-protected amine substrates undergo facile alkoxylation at the γ or δ positions with a range of alcohols, including t-BuOH, to give alkoxylated products. This method features a relatively broad substrate scope for amines and alcohols, inexpensive reagents, and convenient operating conditions. This method highlights the emerging value of unactivated C-H bonds, particularly the C(sp3)-H bond of methyl groups, as functional groups in organic synthesis.

Amino acids as building blocks for the synthesis of substituted 1,2,4-triazoles

We report on the synthesis of 1,2,4-triazoles substituted with 2 or 3 amino acid side chains, using silver benzoate as a key reagent for the cyclization step. A complete study of the optical purity retention during the synthetic process leading to these c

N4-tetradentate dicarboxyamidate/dipyridyl palladium complexes as robust catalysts for the Heck reaction of deactivated aryl chlorides

The utility of palladium(II) complexes of tetradentate dicarboxyamide/ dipyridyl ligands as catalysts for the Heck reaction of deactivated aryl chlorides and olefins was studied. The square-planar palladium complexes were prepared by treatment of the ligands with Pd(OAc)2 in THF at room temperature. Thermogravimetric analysis show that both the palladium complexes have high thermal stability up to 350°C. LiOH·H2O has a pronounced effect on the product yield, while a yield of 74% is obtained by using DMA as a solvent at 160°C in 44 h. The reactions of less reactive aryl chlorides such as 4-chloroanisole, 4-chlorotoluene, and chlorobenzene with styrene and 4-methylstyrene, proceed smoothly and provide good yields. Both palladium complexes are found to be efficient and active for the Heck reaction of deactivated aryl chlorides and olefins.