Lossen Rearrangement by Rh(III)-Catalyzed C-H Activation/Annulation of Aryl Hydroxamates with Alkynes: Access to Quinolone-containing Amino Acid Derivatives

2021 ◽  
Author(s):  
Dmitry A. Petropavlovskikh ◽  
Daria Vorobyeva ◽  
Ivan A. Godovikov ◽  
Sergey E Nefedov ◽  
Oleg A. Filippov ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Robust Method ◽  
Acid Moiety ◽  
Internal Alkynes ◽  
Amino Acid Moiety

A convenient and robust method for the preparation of new CF3-containing 2-quinolones has been developed via Rh(III)-catalyzed C-H activation/Lossen rearrangement/annulation cascade of N-pivaloyloxy-arylamides with internal alkynes bearing α-CF3-α-amino acid moiety...

scholarly journals Synthesis and antimicrobial activity of some novel 1,2-dihydro-[1,2,4]triazolo[1,5-a]pyrimidines bearing amino acid moiety

RSC Advances ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 2905-2916
Author(s):  
Mounir A. A. Mohamed ◽  
Adnan A. Bekhit ◽  
Omyma A. Abd Allah ◽  
Asmaa M. Kadry ◽  
Tamer M. Ibrahim ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Amino Acid ◽  
Green Chemistry ◽  
Antimicrobial Activities ◽  
Amino Acid Derivatives ◽  
Acid Moiety ◽  
Amino Acid Moiety

A new series of [1,2,4]-triazole bearing amino acid derivatives were synthesized under green chemistry conditions and evaluated for their antimicrobial activities.

scholarly journals Acrylamide Formation in Food: A Mechanistic Perspective

2005 ◽  
Vol 88 (1) ◽  
pp. 262-267 ◽  
Author(s):  
Varoujan A Yaylayan ◽  
Richard H Stadler
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Azomethine Ylide ◽  
Significant Progress ◽  
Acid Moiety ◽  
Sugar Moiety ◽  
Acrylamide Formation ◽  
Amino Acid Moiety ◽  
Strecker Aldehyde

Abstract Earliest reports on the origin of acrylamide in food have confirmed asparagine as the main amino acid responsible for its formation. Available evidence suggests that sugars and other carbonyl compounds play a specific role in the decarboxylation process of asparagine, a necessary step in the generation of acrylamide. It has been proposed that Schiff base intermediate formed between asparagine and the sugar provides a low energy alternative to the decarboxylation from the intact Amadori product through generation and decomposition of oxazolidin-5-one intermediate, leading to the formation of a relatively stable azomethine ylide. Literature data indicate the propensity of such protonated ylides to undergo irreversible 1,2-prototropic shift and produce, in this case, decarboxylated Schiff bases which can easily rearrange into E Decarboxylated Amadori products can either undergo the well known β-elimination process initiated by the sugar moiety to produce 3-aminopropanamide and 1-deoxyglucosone or undergo 1,2-elimination initiated by the amino acid moiety to directly generate acrylamide. On the other hand, the Schiff intermediate can either hydrolyze and release 3-aminopropanamide or similarly undergo amino acid initiated 1,2-elimination to directly form acrylamide. Other thermolytic pathways to acrylamide—considered marginal at this stage—via the Strecker aldehyde, acrolein, and acrylic acid, are also addressed. Despite significant progress in the understanding of the mechanistic aspects of acrylamide formation, concrete evidence for the role of the different proposed intermediates in foods is still lacking.

Design, Synthesis and Insecticidal Evaluation of Anthranilic Diamides Containing Optically Pure Amino Acid Moiety

2016 ◽  
Vol 34 (12) ◽  
pp. 1218-1224 ◽  
Author(s):  
Shaa Zhou ◽  
Sha Zhou ◽  
Xuewen Hua ◽  
Wei Wei ◽  
Yongtao Xie ◽  
...  
Keyword(s):  
Amino Acid ◽  
Acid Moiety ◽  
Design Synthesis ◽  
Amino Acid Moiety ◽  
Pure Amino Acid ◽  
Optically Pure

[1.4]Diazepino[6.5-c]chinoline mit L-Aminosäurebaustein — Darstellung und Reaktionen / [1.4]Diazepino[6.5-c]quinolines with L-Amino Acid Moiety — Preparation and Reactions

1987 ◽  
Vol 42 (9) ◽  
pp. 1167-1173 ◽  
Author(s):  
Sabine Bohnert ◽  
Wolf-H. Gündel
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Model Compound ◽  
Acid Moiety ◽  
Quaternary Salts ◽  
Amino Acid Moiety

Quaternary salts of the amides of N-(3-quinolinecarbonyl)-N-alkyl-amino acids (6) cyclise under the influence of base to the title compounds (7). This intramolecular addition is a reaction with high diastereoselectivity, dependent on the amino acid part. 7 disproportionates to 8 and 9. 7 behaves as lipophilic NAD model compound in the reaction with 2-propanol under ZnCl2 catalysis.

Nakinadine A, a Novel Bis-pyridine Alkaloid with a β-Amino Acid Moiety from Sponge Amphimedon sp.

ChemInform ◽  
2007 ◽  
Vol 38 (45) ◽  
Author(s):  
Takaaki Kubota ◽  
Takami Nishi ◽  
Eri Fukushi ◽  
Jun Kawabata ◽  
Jane Fromont ◽  
...  
Keyword(s):  
Amino Acid ◽  
Acid Moiety ◽  
Amino Acid Moiety

Chiral β3-isocyanopropionates for multicomponent synthesis of peptides and depsipeptides containing a β-amino acid fragment

2018 ◽  
Vol 16 (33) ◽  
pp. 5987-5998 ◽  
Author(s):  
Danil P. Zarezin ◽  
Olga I. Shmatova ◽  
Valentine G. Nenajdenko
Keyword(s):  
Amino Acid ◽  
Multicomponent Reactions ◽  
Short Peptides ◽  
Multicomponent Synthesis ◽  
Acid Moiety ◽  
Amino Acid Fragment ◽  
Acid Fragment ◽  
Amino Acid Moiety ◽  
New Type

Chiral β3-isocyanopropionic acids derivatives is a new type of isocyanides for multicomponent reactions. The use of these isocyanides in Ugi and Passerini reactions allows to prepare short peptides and depsipeptides with β-amino acid moiety in the structure.

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