Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• hydroxy groups by the action of an activated ester in the presence of a suitable hydrolase in organic solvents [22][23]. Different authors have shown that activated dicarboxylates are also accepted as acyl donors by these enzymes. As an example, Figure 1 shows the products obtained using divinyl adipate

Surprisingly facile CO₂ insertion into cobalt alkoxide bonds: A theoretical investigation

• Willem K. Offermans,
• Claudia Bizzarri,
• Walter Leitner and
• Thomas E. Müller

Beilstein J. Org. Chem. 2015, 11, 1340–1351, doi:10.3762/bjoc.11.144

• explored in several studies. Rieger et al. studied the mechanisms of the copolymerisation by homogeneous chromium(III)– and aluminium(III)–salen complexes and by heterogeneous zinc-dicarboxylates [30][31]. Experimental work on the chromium(III)– and aluminium(III)–salen complexes was combined with a

• feasible. In mechanistic studies on zinc dicarboxylates and their application in the heterogeneously catalysed copolymerisation of CO2 and epoxides a bimetallic mechanism was proposed [31]. As post-modification of the prepared catalysts with water proved to be important for the activity of the catalysts

• alternating polycarbonates, polyethercarbonates or cyclic carbonates. Epoxide and CO2 copolymerisation by homogeneous Cr(III)– and Al(III)–salen complexes. Heterogeneous zinc dicarboxylates for the copolymerisation of CO2 and epoxides. (* = End group of polymer chain). Backbiting mechanism for the formation

Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

• Grzegorz Mlostoń,
• Paulina Grzelak,
• Maciej Mikina,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2015, 11, 576–582, doi:10.3762/bjoc.11.63

• rearranged products (Pummerer-type rearrangement) upon treatment of 1H-2-benzothiopyran-3,4-dicarboxylates of type 4 with an equimolar amount of mCPBA. Conclusion The present study shows that hetaryl thioketones react with activated acetylenecarboxylates in a hetero-Diels–Alder reaction followed by the 1,3

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

• Volodymyr V. Tkachenko,
• Elena A. Muravyova,
• Sergey M. Desenko,
• Oleg V. Shishkin,
• Svetlana V. Shishkina,
• Dmytro O. Sysoiev,
• Thomas J. J. Müller and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

• , Světlik et al. studied the Biginelli-type condensation of 2-hydroxybenzaldehyde with urea (thiourea) and dialkyl acetone-1,3-dicarboxylates as active methylene components [16]. Unexpectedly, the reaction with salicylaldehyde furnished two different products depending on the ester alkyl group (Scheme 2

Silver and gold-catalyzed multicomponent reactions

• Giorgio Abbiati and
• Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

• keteneimines 57 [77] or in [3 + 3] processes with dimethyl cyclopropane-1,1-dicarboxylates 59 [78]. Both these reactions are co-catalyzed, the former by silver triflate and copper bromide and the latter by silver triflate and nickel(II) perchlorate (Scheme 30 and Scheme 31). In [3 + 2]-cycloaddition reactions

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

• Sándor B. Ötvös,
• Ádám Georgiádes,
• István M. Mándity,
• Lóránd Kiss and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172

• cases; Table 1, entries 3 and 4). 1,4,5-Trisubstituted 1,2,3-triazoles are of notable importance in drug discovery. For example, several 1,2,3-triazole-4,5-dicarboxylates display significant antituberculotic activity in vitro [69]. Thus, a nonterminal alkyne, diethyl acetylenedicarboxylate, was

• subjected to CF CuAAC with the azido-functionalized β-amino acid derivatives 11–14 as reaction partners. 1,4,5-Trisubstituted 1,2,3-triazole dicarboxylates 19–22 were obtained in excellent yields (>96%) under both conditions A and B (Table 1, entries 5–8). In this set of CF syntheses, no significant

Enaminones in a multicomponent synthesis of 4-aryldihydropyridines for potential applications in photoinduced intramolecular electron-transfer systems

• Nouria A. Al-Awadi,
• Maher R. Ibrahim,
• Mohamed H. Elnagdi,
• Elizabeth John and
• Yehia A. Ibrahim

Beilstein J. Org. Chem. 2012, 8, 441–447, doi:10.3762/bjoc.8.50

• -dihydropyridine-3,5-dicarboxylates have been investigated as useful organic dyads for the vectorial transport of energy or charge transfer [7][8] (Scheme 1). A few photochemical applications of dyads of this structure have been demonstrated including their use in photosensitive polymers [9][10], in biosensors or

• compounds 2j, 4a, 6a–f and 7a,b after excitation at their absorption λmax in the range of 383–406 nm in acetonitrile (1 × 10−4 M). ORTEP of compound 15d. 2,6-Dihydropyridine-3,5-dicarboxylates as useful organic dyads. Synthesis of dihydropyridine derivatives from enaminones. Dihydropyridine derivatives 4–7

Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters

• Satish S. More,
• T. Krishna Mohan,
• Y. Sateesh Kumar,
• U. K. Syam Kumar and
• Navin B. Patel

Beilstein J. Org. Chem. 2011, 7, 831–838, doi:10.3762/bjoc.7.95

• /bjoc.7.95 Abstract A novel synthetic methodology has been developed for the synthesis of diethyl 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates (also called 2-substituted pyrroline-4,5-dihydro-3,3-dicarboxylic acid diethyl esters) by iodide ion induced ring expansion of 2

• substituted novel pyrroline derivatives have been synthesized by this methodology and the products can be used as key intermediates in the synthesis of substituted pyrrolines, pyrroles and pyrrolidines. Keywords: 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates; aziridine; N

• /heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates. The synthesis of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters was carried out by nucleophilic displacement by aziridine of the chloro atom from electron-poor activated 2-(1-alkyl/aryl/heteroaryl-1

An easy assembled fluorescent sensor for dicarboxylates and acidic amino acids

• Xiao-bo Zhou,
• Yuk-Wang Yip,
• Wing-Hong Chan and
• Albert W. M. Lee

Beilstein J. Org. Chem. 2011, 7, 75–81, doi:10.3762/bjoc.7.11

• for sensing dicarboxylates. Their binding affinities toward dicarboxylates, aspartate and glutamate have been investigated in acetonitrile solution by fluorescence titration experiments. Both fluorescent sensors exhibited some ability to discriminate the antipodal forms of aspartate and glutamate

• roles of anions in many chemical and biological processes [1][2][3][4][5]. Being the key structural moieties of many bioactive molecules such as amino acids and proteins, dicarboxylates are one of the most attractive targets for anion recognition and sensing. In addition, dicarboxylates are essential

• (i.e., chromophore or fluorophore) as sensing probes for dicarboxylates [8][9][10][11][12][13]. Additionally, chiral recognition of carboxylates has been actively explored in the sensor field [14][15][16]. By using cholic acid as the molecular scaffold for the construction of sensing probes, we have