Bismuth-catalyzed arylation of ethyl glyoxylate with aniline via N–H insertion

Glycine derivatives such as ethyl 2-(4-aminophenyl)-2-(phenylamino) acetate is an exciting and essential non-proteinogenic class of amino acids. Herein, we report an efficient and novel route to synthesize glycine derivatives using ethyl glyoxylate, aniline, and its derivatives catalyzed by bismuth...

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Bibliographic Details
Published inMolecular diversity Vol. 27; no. 1; pp. 167 - 175
Main Authors Riyaz, Mohd. Aamir Bin, Premkumar, G., Swu, Toka
Format Journal Article
LanguageEnglish
Published Cham Springer International Publishing 01.02.2023
Springer Nature B.V
Subjects
Aniline Compounds - chemistry
Antibiotics
Biochemistry
Biomedical and Life Sciences
Bismuth - chemistry
Catalysis
Glycine - chemistry
Glyoxylates
Life Sciences
Organic Chemistry
Original Article
Pharmacy
Polymer Sciences
Solvents
Ethylglyoxylate
Bismuth chloride
Aniline
N–H insertion
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Summary:Glycine derivatives such as ethyl 2-(4-aminophenyl)-2-(phenylamino) acetate is an exciting and essential non-proteinogenic class of amino acids. Herein, we report an efficient and novel route to synthesize glycine derivatives using ethyl glyoxylate, aniline, and its derivatives catalyzed by bismuth salts. In our scheme, mild, non-toxic, and commercially viable reagents were utilized. The synthesized moieties were characterized by ESI-MASS, 1 H-NMR, 13 C-NMR, and XRD techniques. The target glycine derivatives were successfully obtained with a maximum yield of 87%. Moreover, the reaction is very green as water is the only byproduct. Graphical abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-022-10411-x