Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• Biology and Konstanz Research School Chemical Biology (KoRS-CB), Universitätsstraße 10, 78457 Konstanz, Germany 10.3762/bjoc.10.232 Abstract Monitoring glycoconjugates has been tremendously facilitated by the development of metabolic oligosaccharide engineering. Recently, the inverse-electron-demand

• higher fluorescence staining of cell-surface glycoconjugates, the glucosamine derivative gave higher labeling efficiency with protein preparations containing also intracellular proteins. Keywords: bioorthogonal chemistry; carbohydrates; cyclopropenes; inverse-electron-demand Diels-Alder reactions

• strain-promoted [11][12]). Since the initial reports from 2008 [13][14][15], more and more laboratories successfully employ the inverse-electron-demand Diels–Alder (DAinv) reaction as a bioorthogonal ligation reaction for different applications [16][17][18]. In the meantime, the DAinv reaction has also

Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM₃-lactone mimetic

• Renato Ribeiro-Viana,
• Elena Bonechi,
• Javier Rojo,
• Clara Ballerini,
• Giuseppina Comito,
• Barbara Richichi and
• Cristina Nativi

Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

• unit of 6 was efficiently performed relying on a totally diastereoselective inverse electron-demand [4 + 2] hetero-Diels–Alder reaction , as described in [31]. The synthesis of compound 5 is depicted in Scheme 1. The mimetic 6 was deprotected with sodium carbonate at room temperature. Without further

Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

• Amitabh Jha,
• Ting-Yi Chou,
• Zainab ALJaroudi,
• Bobby D. Ellis and
• T. Stanley Cameron

Beilstein J. Org. Chem. 2014, 10, 848–857, doi:10.3762/bjoc.10.81

• ; cyclization; Diels–Alder; inverse electron demand; N-acyliminium ion; tert-enamide; Introduction Fused indoline, isoindoline, quinoline and isoquinoline substructures are found in many natural products and bioactive synthetic compounds (Figure 1). For example, nuevamine is a naturally-occurring isoindolo[1,2

• major highlight of this work. Results and Discussion Our literature search revealed that although tert-enamides have been used as dienophiles for the Povarov reaction to build 1,2,3,4-tetrahydroquinoline blocks [25][26][37], there were no reports of their usage in the inverse electron demand hetero

• the dienophile, at least two regioisomers can be visualized for these compounds. Based on our characterization results, only one regioisomer, where the substitution was at position 5 of the isoindoloquinoline ring, was exclusively formed in these reactions. Inverse-electron demand hetero-Diels–Alder

Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions

• Salah Fadel,
• Youssef Hajbi,
• Mostafa Khouili,
• Said Lazar,
• Franck Suzenet and
• Gérald Guillaumet

Beilstein J. Org. Chem. 2014, 10, 282–286, doi:10.3762/bjoc.10.24

• electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels–Alder

• reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route. Keywords: inverse-electron-demand Diels–Alder reaction; microwave irradiation; naphthyridin-2(1H)-ones; Sonogashira cross-coupling; 1,2,4-triazine; Introduction 1,8-Naphthyridine derivatives are an important

• -demand Diels–Alder reaction under microwave irradiation [22][23][24]. The use of 1,2,4-triazines in inverse electron-demand Diels–Alder reactions proved to be an efficient strategy for the construction of various heterocyclic compounds [25][26][27], such as azacarbazoles [28][29][30][31][32][33

Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

• Ludovic Eberlin,
• Fabien Tripoteau,
• François Carreaux,
• Andrew Whiting and
• Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

• ]-cycloadditons, can further be engaged in an allylation reaction that significantly increased the structural diversity of the final products (Scheme 24). As 3-boronoacrolein esters which have been used in metal-catalyzed inverse electron demand [4 + 2]-cycloadditions, 32 reacted with ethyl vinyl ether in the

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

• Sebastian Krüger and
• Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

• was achieved using TBAF, followed by formation of a vinyl triflate and Stille coupling with tributyltin hydride. The oxidation state of the remaining ester was adjusted to the corresponding aldehyde, followed by a Lewis acid-catalyzed intramolecular inverse-electron-demand hetero-Diels–Alder reaction

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

• Zhiyuan Ma,
• Feng Ni,
• Grace H. C. Woo,
• Sie-Mun Lo,
• Philip M. Roveto,
• Scott E. Schaus and
• John K. Snyder

Beilstein J. Org. Chem. 2012, 8, 829–840, doi:10.3762/bjoc.8.93

• Intramolecular inverse electron demand cycloadditions of isatin-derived 1,2,4-triazines with acetylenic dienophiles tethered by amidations or transesterifications proceed in excellent yields to produce lactam- or lactone-fused α-carbolines. Beginning with various isatins and alkynyl dienophiles, a pilot-scale

• library of eighty-eight α-carbolines was prepared by using this robust methodology for biological evaluation. Keywords: α-carboline; chemical diversity; inverse electron demand Diels–Alder; isatin; pyrido[2,3-b]indole; 1,2,4-triazine; Introduction In comparison with the well-known β-carbolines, α

• library of annulated α-carboline structures 6 could be prepared by the intramolecular inverse electron demand Diels–Alder reaction (IEDDA) of isatin-derived 1,2,4-triazines 7 with tethered electron-rich dienophiles (Scheme 1) [69]. Inverse electron demand Diels–Alder cycloadditions employing electron

Novel loop-like aromatic compounds: a further step on the road to nanobelts and nanotubes

• Venkataramana Rajuri,
• Dariush Ajami,
• Gaston R. Schaller,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2010, 6, No. 30, doi:10.3762/bjoc.6.30

• ). The olefinic double bonds are not involved. The central olefinic double bond in 1 is not activated by electron withdrawing substituents and therefore was reacted with an electron-poor diene in a Diels–Alder reaction with inverse electron demand. 2,3,4,5-Tetrachlorothiophene-1,1-dioxide (10) is one of

An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium- catalyzed multi- component domino reaction

• Dipak Prajapati and
• Mukut Gohain

Beilstein J. Org. Chem. 2006, 2, No. 11, doi:10.1186/1860-5397-2-11

• ], we have investigated a new, simple and efficient synthesis of novel fused pyrimidines based on inverse electron-demand Diels-Alder reaction using ethyl vinyl ether/dihydrofuran and α,β-ethylenic ketones formed in situ as heterodienes in presence of 1 mol% of indium(III) trichloride (Scheme 1). This

• aldehyde 2 with the 1,3-dimethylbarbituric acid,[37] which is highly activated due to the presence of the electron withdrawing group. It can, therefore, react with the ethyl vinyl ether at room temperature, to provide the cycloadduct 5 in a hetero-Diels-Alder reaction with inverse electron-demand. [38][39

• , which makes it a useful process for the synthesis of cis-fused furopyrano [2,3-d]pyrimidines and pyrano [2,3-d]pyrimidines. Reagents and conditions: i) 1 mol% InCl3, acetonitrile:water (3:1) Reagents and conditions: i) 1 mol% InCl3, room temperature Inverse electron-demand hetero-Diels-Alder reaction