97458-28-1Relevant academic research and scientific papers
Green synthesis of new chiral 1-(arylamino)imidazo-[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
Bouzayani, Nadia,Kra?em, Jamil,Marque, Sylvain,Kacem, Yakdhane,Carlin-Sinclair, Abel,Marrot, Jér?me,Hassine, Béchir Ben
supporting information, p. 2923 - 2930 (2018/12/13)
New chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-dione derivatives were obtained in good to excellent yields via the cyclocondensation of 2-formylbenzoic acid and various α-amino acid arylhydrazides using water as the solvent in the presence of sodium
Synthesis of new chiral bis-imidazolidin-4-ones: Comparison between the classic method and green chemistry conditions
Bouzayani, Nadia,Talbi, Wassima,Marque, Sylvain,Kacem, Yakdhane,Hassine, Béchir Ben
, p. 229 - 239 (2018/07/05)
Novel bis-imidazolidin-4-ones were synthesized in moderate to good yields through the cyclocondensation of o-, m-and p-phthalaldehydes with various substituted phenylhydrazides. These nitrogenated cyclic compounds were prepared via green chemistry conditi
Enantiopure Schiff bases of amino acid phenylhydrazides: Impact of the hydrazide function on their structures and properties
Bouzayani, Nadia,Marque, Sylvain,Djelassi, Brahim,Kacem, Yakdhane,Marrot, Jér?me,Ben Hassine, Béchir
, p. 6389 - 6398 (2018/04/23)
A rapid and eco-friendly synthesis of new enantiopure Schiff bases 5a-e was performed from various α-amino acid phenylhydrazides and 2-hydroxynaphthaldehyde using microwave or ultrasound irradiation in yields ranging from 57 to 75%. These imines were char
Solvent-free synthesis of new chiral 3-phenylamino-3,5-dihydro-4h-imidazol- 4-one derivatives from α-amino acid phenylhydrazides
Kacem, Yakdhane,Hassine, Bechir Ben
, p. 197 - 207 (2014/02/14)
Enantiopure 2,5-disubstituted 3-phenylamino-3,5-dihydro-4Himidazol- 4-one derivatives were obtained in good to excellent yields by condensation of chiral α-amino acid phenylhydrazides and triethyl orthoesters in the presence of dry acetic acid as catalyst
A convenient procedure for the synthesis of chiral 6,7-dihydroxy-1- phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones
Kacem, Yakdhane,Hassine, Bechir Ben
, p. 252 - 257 (2014/03/21)
The cyclocondensation reactions between l-α-amino acid phenylhydrazides and 2,3-O-isopropylidene-l-erythruronolactone in the presence of a catalytic amount of p-toluenesulfonic acid afforded diastereomerically pure (3S,6R,7R,7aS)-3-substituted-6,7-isoprop
Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis
Voelkert, Martin,Koul, Surrinder,Mueller, Gernot H.,Lehnig, Manfred,Waldmann, Herbert
, p. 6902 - 6910 (2007/10/03)
The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14.18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodology are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo- and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive methionine residues was not observed. These features make the methodology suitable for the synthesis of sensitive peptide conjugates. Mechanistic data suggest that the hydrolysis of the oxidized adducts proceeds by a free-radical mechanism.
New heterocycles from the reaction between some natural α-amino acid hydrazides and formaldehyde
Verardo, Giancarlo,Toniutti, Nicoletta,Gorassini, Andrea,Giumanini, Angelo G.
, p. 2943 - 2948 (2007/10/03)
The ring forming condensation between some natural α-amino acid phenylhydrazides (1) and aqueous formaldehyde (2) has opened a novel synthetic route to hexahydro-1,2,4-triazin-6-one derivatives (3). Polycyclic systems were obtained from the same reaction carried out with L-aspartic acid 1,4-bis(2-phenylhydrazide) (1d), L-histidine phenylhydrazide (1e) and L- tryptophan phenylhydrazide (1f) which gave perhydro-4,6-dioxo-2,8- diphenyl[1,2,4]triazino[4,5-d][1,2,4]triazepine (5) perhydro-1-oxo-3- phenylimidazo[5,4-d][1,2,4]triazino[4,5-a]pyridine (7) and 1,2,3-H-3-(2- phenylcarbazoyl)-β-carboline (8), respectively. Substrates 1 were conveniently obtained by direct reaction of phenylhydrazine with L-α-amino acid esters retaining the original chirality.
