178918-29-1Relevant articles and documents
Synthesis of chlorins by Diels-Alder cycloadditions of pheophorbide a and its derivatives
Bri?, Anamarija,Marini?, ?eljko,Chen, Zhi-Long,Margeti?, Davor
, p. 991 - 994 (2015)
The Diels-Alder reaction was exploited for the preparation of novel long-wavelength chlorin photodynamic therapy photosensitizers. The styryl group and furan carboxamide substituents were used as diene components in [4+2] cycloaddition functionalizations.
Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines
Ingale, Ajit P.,Garad, Dnyaneshwar N.,Ukale, Dattatraya,Thorat, Nitin M.,Shinde, Sandeep V.
supporting information, p. 3791 - 3804 (2021/11/04)
Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.
Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst
Awasthi, Amardeep,Mukherjee, Anagh,Singh, Mandeep,Rathee, Garima,Vanka, Kumar,Chandra, Ramesh
, (2020/05/14)
An efficient approach for the Chemoselective N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation of side products like urea, oxazolidinone, isocyanate, and N, N-di-Boc derivatives makes the present protocol desirable.
Synthesis method of 5-aminolevulinic acid hydrochloride
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Paragraph 0051; 0052; 0075; 0076, (2019/04/26)
The invention relates to a synthesis method of 5-aminolevulinic acid hydrochloride (5-ALA), furfuryl amine (2-furylamine) is used as an initial raw material, and the target product is synthesized through four steps of amino protection, oxidation reaction, reduction reaction and hydrolysis decarboxylation. Reagents used in the synthesis method are low in price, easy to obtain, and environment-friendly and the operation is simple.
Facile fabrication of fast recyclable and multiple self-healing epoxy materials through diels-alder adduct cross-linker
Kuang, Xiao,Liu, Guoming,Dong, Xia,Liu, Xianggui,Xu, Jianjun,Wang, Dujin
, p. 2094 - 2103 (2015/08/11)
J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2094-2103 A reversibly cross-linked epoxy resin with efficient reprocessing and intrinsic self-healing has been prepared from a newly synthesized diamine Diels-Alder (DA) adduct cross-linker and a commercial epoxy oligomer. The methodology developed in this work takes smart and environmentally benign epoxy to the next level of simplicity and provides new insights in the modification of traditional engineering plastics as a functional material.
Degradable conjugates from oxanorbornadiene reagents
Kislukhin, Alexander A.,Higginson, Cody J.,Hong, Vu P.,Finn
supporting information; experimental part, p. 6491 - 6497 (2012/05/07)
Oxanorbornadienedicarboxylate (OND) reagents were explored for purposes of binding and releasing drugs from serum albumins as representative macromolecular carriers. Being highly reactive Michael acceptors, ONDs form adducts with thiols and amines, which then undergo retro-Diels-Alder fragmentation. A study of more than 30 model adducts revealed a number of modifications that can be used to influence adduct stability. For the most reactive OND linkers, the labeling of the single available bovine serum albumin (BSA) cysteine residue was complete within minutes at a mid-micromolar concentration of reactants. While a selectivity of greater than 1000-fold for thiol over amine was observed with model amino acids, the labeling of protein amines with ONDs is fast enough to be practical, as demonstrated by the reaction with thiol-depleted BSA. The OND-amine adducts were found to be up to 15 times more stable than OND-thiol adducts, and to be sensitive to acid by virtue of a stereochemically dependent acceleration of cycloreversion. The release rate of fluorescent cargo from serum albumins was tuned by selecting the coupling partners: the available half-lives ranged from 40 min to 7 days at 37 °C. Such versatility of release profiles from protein carriers, controlled by the nature of the OND linkage, is a useful addition to the drug delivery toolbox.
Nonsolvent application of ionic liquids: Organo-catalysis by 1-alkyl-3-methylimidazolium cation based room-temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency
Sarkar, Anirban,Roy, Sudipta Raha,Parikh, Naisargee,Chakraborti, Asit K.
experimental part, p. 7132 - 7140 (2011/10/08)
1-Alkyl-3-methylimidazolium cation based ionic liquids efficiently catalyze N-tert-butyloxycarbonylation of amines with excellent chemoselectivity. The catalytic role of the ionic liquid is envisaged as "electrophilic activation" of di-tert-butyl dicarbonate (Boc2O) through bifurcated hydrogen bond formation with the C-2 hydrogen of the 1-alkyl-3-methylimidazolium cation and has been supported by a downfield shift of the imidazolium C-2 hydrogen of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim][NTf2]) from δ 8.39 to 8.66 in the presence of Boc2O in the 1H NMR and a drastic reduction of the catalytic efficiency with 1-butyl-2,3-dimethylimidazolium ionic liquids that are devoid of the C-2 hydrogen. The differential time required for reaction with aromatic and aliphatic amines has offered means for selective N-t-Boc formation during inter and intramolecular competitions. Preferential N-t-Boc formation with secondary aliphatic amine has been achieved in the presence of primary aliphatic amine. Comparison of the catalytic efficiency for N-t-Boc formation with a common substrate revealed that [bmim][NTf2] is superior to the reported Lewis acid catalysts.
One-pot synthesis of α-amino acids from imines through CO2 incorporation: An alternative method for strecker synthesis
Mita, Tsuyoshi,Chen, Jianyang,Sugawara, Masumi,Sato, Yoshihiro
supporting information; experimental part, p. 1393 - 1396 (2011/04/22)
Itas a gas: A novel one-pot process for the synthesis of α-amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl.
NOVEL CARBAPENEM DERIVATIVES
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Page/Page column 13, (2010/05/13)
The present invention relates to novel carbapenem derivatives and belongs to pharmaceutical field. Specifically, the present invention relates to the compounds as represented by formulae (1) and (2), pharmaceutically acceptable salts, hydrolysable esters,
Palladium-catalysed direct 5-arylation of furfurylamine or 2-(aminoalkyl)-thiophene derivatives
Roger, Julien,Doucet, Henri
experimental part, p. 4412 - 4425 (2010/10/19)
The palladium-catalysed direct 5-arylation of furan or thiophene derivatives bearing CH2NHR substituents (with. R = COMe or CO 2tBu) generally proceeds in good yields by using a catalysts loading of only 0.1-2 mol-%. A wide range of functions such as acetyl, propionyl, formyl, ester, nitrile, trifluoromethyl or fluoro on the aryl bromide is tolerated. Higher yields were generally obtained in the presence of electron-deficient aryl bromides than with, electron-rich aryl bromides.
