1795-96-6Relevant articles and documents
Synthesis of pharmacophores containing a prolinate core using a multicomponent 1,3-dipolar cycloaddition of azomethine ylides
Selva, Elisabet,Castelló, Luis M.,Mancebo-Aracil, Juan,Selva, Verónica,Nájera, Carmen,Foubelo, Francisco,Sansano, José M.
, p. 6840 - 6846 (2017)
A multicomponent 1,3-dipolar cycloaddition between heterocyclic aldehydes, amino esters and dipolarophiles is efficiently promoted by silver acetate as catalyst, and depending on the nature of the heterocycle and its reactivity the reaction requires 70 °C or rt to complete. Selected pharmacophores anchored to a formyl group are chromone, 5-methoxyindole, pyridoxal surrogates and a very attractive uracyl derivative. The preference of each tested amino esters towards different dipolarophiles is discussed. At the end, a selective reduction of the ester group allows to obtain a very interesting dideoxiazanucleoside derivative.
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Mason,Winder
, p. 191 (1894)
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Dynamic Kinetic resolution of α-amino acid esters in the presence of aldehydes
Schichl, Daniel A.,Enthaler, Stephan,Holla, Wolfgang,Riermeier, Thomas,Kragl, Udo,Beller, Matthias
, p. 3506 - 3512 (2008)
A convenient procedure for the racemization of α-amino acid esters in the presence of catalytic amounts of salicylaldehydes is described. The combination of this racemization protocol with lipase-catalyzed ester hydrolysis allows successful dynamic kinetic resolution of various α-amino acid esters. The corresponding α-amino acids are obtained in high yield and optical purity. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Dichloromeldrum's acid (DiCMA): A practical and green amine dichloroacetylation reagent
Heard, David M.,Lennox, Alastair J.J.
supporting information, p. 3368 - 3372 (2021/05/06)
Dichloromeldrum's acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.
Stereospecific Synthesis of 3,4-Dihydro-2 H-naphtho-1,4-oxazin-2-ones by Unification of Benzoxepine-4-carboxylates with Chiral Amino Acid Ethyl Esters
Bhimapaka, China Raju,Kasagani, Veera Prasad,Kurma, Siva Hariprasad
supporting information, p. 2976 - 2983 (2020/03/23)
A novel and efficient stereocontrolled method has been developed for the preparation of chiral 3,4-dihydro-2H-naphtho[1,2-b][1,4]oxazin-2-ones by the reaction of benzoxepine-4-carboxylates with chiral amino acid ethyl esters for the first time. The chiral 3,4-dihydro-2H-naphtho-1,4-oxazinones have been achieved in one step by the formation of C-N, C-C, and C-O bonds.