54535-21-6Relevant academic research and scientific papers
Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones
Pal, Arpal,Koduri, Naga D.,Wang, Zhiguo,Quiroz, Erika Lopez,Chong, Alexandra,Vuong, Matthew,Rajagopal, Nisha,Nguyen, Michael,Roberts, Kenneth P.,Hussaini, Syed R.
supporting information, p. 586 - 589 (2017/01/16)
The development of operationally simple and cost-effective methods for C[sbnd]C bond formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted α-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary, secondary and tertiary thioamides all give enanminones when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, α-diazoketoamides, α-diazoesteramides, α-diazoketosulfones and α-diazomonoketones.
2,2-Bis(ethoxycarbonyl)vinyl (BECV) as a versatile amine protecting group for selective functional-group transformations
Ilangovan, Andivelu,Kumar, Rajendran Ganesh
body text, p. 2938 - 2943 (2010/07/02)
A 2,2-Bis(ethoxycarbonyl) vinyl- (BECV) group was used for the selective protection of amines at room temperature in the presence of potentially interfering functional groups such as OH, SH, COOH as well as other NH 2 groups. Several functional group transformations such as esterification, O-alkylation, O-acylation, N-alkylation, N-acylation, S-alkylation can selectively be carried out in the presence of the BECV group. The selective deprotection of the BECV group was achieved in a short time using ethylenediamine at room temperature while several other functional groups such as benzoate, aliphatic esters, amides and ethers remain intact. The BECV group shows orthogonal stability against the common protecting groups such as Fmoc, Cbz and Boc.
A clay catalyzed method for diethyl 2,2,2- trichloroethylidenepropanedioate, an efficient intermediate for the synthesis of enamino esters
Deshmukh,Panse,Bhawal
, p. 1801 - 1809 (2007/10/03)
An improved high yielding procedure for diethyl 2,2,2- trichloroethyledinepropanedioate (3) using montmorillonite K-10 catalyst has been described. Various diethyl (substituted aminomethylene)propanedioates (6a-j) have been synthesised in excellent yields starting from propanedioate (3) via addition products (5a-j).
Some Approaches to the Synthesis of Kainic Acid
Husinec, Suren,Porter, Alexander E. A.,Roberts, James S.,Strachan, Calum H.
, p. 2517 - 2522 (2007/10/02)
A strategy for the synthesis of the anthelmintic kainic acid is described, involving an investigation of the cycloaddition reactions of some azomethine ylides obtained from the thermal ring opening of aziridines and 4,5-dihydro-1,2,3-triazoles, with
Vibrational Spectroscopy and Conformations of 2-Alkoxycarbonyl-3-aminoacrylic Esters
Gomez-Sanchez, Antonio,Sempere, Eugenia,Bellanato, Juana
, p. 561 - 570 (2007/10/02)
The i.r., Raman, and 1H n.m.r. spectra of 2-alkoxycarbonyl-3-aminoacrylic esters (IV; R1=H, alkyl, aryl) and those of their N-deuteriated derivatives show that these substances exist in the enamino-ester form with a strong intramolecular hydrogen bond between the cis-NH (or -ND) and CO2R2 groups.Some complexities in the i.r. and Raman bands, and their dependence on solvent polarity, temperature, and aggregation state, indicate the existence of rotational isomerism: conformers (IVa and b) predominate in non-polar media; an additional rotamer (IVd) is also probably present in polar solvents.Conformation (IVb) is preferred in the solid state.Some features of the ν(C=O) bands suggest a weak vibrational coupling between the carbonyls.The validity of the criteria established by Smith and Taylor to ascertain the planarity of these and related substances is discussed, and no significant difference in this respect is considered to exist between compounds (IV) with primary and secondary amino-groups.
