One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and α-bromoketones

2019 ◽  
Vol 17 (11) ◽  
pp. 3040-3047
Author(s):  
Jia-Yun Haung ◽  
Indrajeet J. Barve ◽  
Chung-Ming Sun
Keyword(s):  
Amino Acid ◽  
Multicomponent Reaction ◽  
Methyl Esters ◽  
Amino Acid Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Methyl ◽  
Acid Esters ◽  
Amino Acid Methyl Esters

A one-pot multicomponent reaction for assembling substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones has been discovered.

Chiral recognition of amino-acid esters by a glucose-derived macrocyclic receptor

2021 ◽  
Author(s):  
Pit Dominique ◽  
Martin Schnurr ◽  
Bartosz Lewandowski
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Chiral Recognition ◽  
Methyl Esters ◽  
Aqueous Environment ◽  
Amino Acid Esters ◽  
Acid Methyl ◽  
Wide Range ◽  
Acid Esters ◽  
Amino Acid Methyl Esters

We report a glucose-based crown ether capable of chiral recognition of a wide range of amino-acid methyl esters in aqueous environment. The enantioselectivities towards amino-acids with extended hydrophobic side chains...

Destruction of intracellular and isolated Leishmania mexicana amazonensis amastigotes by amino acid amides

Parasitology ◽  
1988 ◽  
Vol 96 (2) ◽  
pp. 289-296 ◽  
Author(s):  
M. Rabinovitch ◽  
V. Zilberfarb
Keyword(s):  
Amino Acid ◽  
Methyl Ester ◽  
Methyl Esters ◽  
Hydrolytic Enzymes ◽  
Amino Acid Esters ◽  
Leishmania Mexicana ◽  
Acid Methyl ◽  
Hydrolysis Of ◽  
Acid Esters ◽  
Amino Acid Methyl Esters

SummaryL-amino acid esters such as leucine methyl ester (Leu-OMe) destroy Leishmania mexicana amazonensis amastigotes by a mechanism which may involve hydrolysis of the compounds by parasite enzymes. Moreover, several esters (e.g. Ile-OMe) prevent the killing of parasites by Leu-OMe, perhaps by inhibition of the hydrolytic enzymes. We show here that certain amino acid amides are also leishmanicidal. Killing of Leishmania within macrophages was assessed microscopically, and that of isolated amastigotes was measured by reduction of the tetrazolium MTT. Amino acid amides were generally less active than the methyl esters and several were more toxic to the macrophages, as determined by inspection of Giemsa-stained preparations. Ranks of activity of the amides on isolated amastigotes were Trp > Leu > Phe > Met > Tyr. The amides of Ala, Gly, Val, Ile, His and D-Leu were inactive. This pattern of activity is similar to that of amino acid methyl esters. Ile-NH2 and a few other amides protected intracellular as well as isolated parasites from killing by Leu-OMe. Conversely, Ile-OMe reduced the toxicity of Leu-NH2 for isolated amastigotes. None of the esters or amides assayed prevented the destruction of Leishmania by Trp-NH2. The results are compatible with the view that amino acid esters and amides may be recognized by the same or similar parasite enzymes.

CuII/TEMPO-Promoted One-Pot Synthesis of Highly Substituted Pyrimidines from Amino Acid Esters

2014 ◽  
Vol 20 (52) ◽  
pp. 17311-17314 ◽  
Author(s):  
Nini Zhou ◽  
Tao Xie ◽  
Zhongle Li ◽  
Zhixiang Xie
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters

One-Pot Synthesis of α-Halo β-Amino Acid Derivatives via the Difunctional Coupling of Ethyl α-Diazoacetate with Silyl Halides and N,O-Acetals or Aromatic Tertiary Amines

Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1823-1832 ◽  
Author(s):  
Norio Sakai ◽  
Kazuki Sasaki ◽  
Hiroki Suzuki ◽  
Yohei Ogiwara
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
Tertiary Amines ◽  
One Pot ◽  
Metal Free ◽  
Reaction Intermediate ◽  
One Pot Synthesis ◽  
Acid Esters ◽  
Three Component Coupling

The difunctionalization of ethyl α-diazoacetate (EDA) using silyl halides as a nucleophile and N,O-acetals as an electrophile under metal-free conditions is described. This process undergoes a novel three-component coupling (3-CC) reaction using EDA, which leads to a one-pot preparation of α-halo β-amino acid esters. Also, this protocol could be adapted to accept an electrophile composed of aromatic tertiary amines. In both 3-CC reactions, the key reaction intermediate is an iminium intermediate that can be easily and effectively generated either from N,O-acetals or from aromatic tertiary amines.

Organocatalytic Synthesis ofN-Phenylisoxazolidin-5-ones and a One-Pot Synthesis of β-Amino Acid Esters

2008 ◽  
Vol 10 (5) ◽  
pp. 953-956 ◽  
Author(s):  
Jayasree Seayad ◽  
Pranab Kumar Patra ◽  
Yugen Zhang ◽  
Jackie Y. Ying
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters

ChemInform Abstract: CuII/TEMPO-Promoted One-Pot Synthesis of Highly Substituted Pyrimidines from Amino Acid Esters.

ChemInform ◽  
2015 ◽  
Vol 46 (21) ◽  
pp. no-no
Author(s):  
Nini Zhou ◽  
Tao Xie ◽  
Zhongle Li ◽  
Zhixiang Xie
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters

ChemInform Abstract: Organocatalytic Synthesis of N-Phenylisoxazolidin-5-ones and a One-Pot Synthesis of β-Amino Acid Esters.

ChemInform ◽  
2008 ◽  
Vol 39 (32) ◽  
Author(s):  
Jayasree Seayad ◽  
Pranab Kumar Patra ◽  
Yugen Zhang ◽  
Jackie Y. Ying
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters

“One-Pot” Methylation ofN-Nosyl-α-amino Acid Methyl Esters with Diazomethane and Their Coupling To PrepareN-Methyl Dipeptides

2003 ◽  
Vol 68 (19) ◽  
pp. 7416-7421 ◽  
Author(s):  
Maria Luisa Di Gioia ◽  
Antonella Leggio ◽  
Adolfo Le Pera ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
...  
Keyword(s):  
Amino Acid ◽  
Methyl Esters ◽  
One Pot ◽  
Acid Methyl ◽  
Amino Acid Methyl Esters
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