Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability

• Malamatenia D. Manouilidou,
• Yannis G. Lazarou,
• Irene M. Mavridis and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 774–783, doi:10.3762/bjoc.10.73

• dissolution of 2 or 3 were observed evidently due to secondary reactions leading to a lower yield for the ligation step. Monomer 4 and dimer 6 displayed a single 31P NMR signal at 35.2 ppm and the correct mass in MALDI–TOF MS. Reaction of 4 with mono(6-15N-amino-6-deoxy)-β-CD under typical amide coupling

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

• , thioacetic acid and 4-methoxy-phenylethylamine (also as chiral auxiliary) provided the corresponding Ugi product 138 in 60% yield (dr 1:1). Chiral separation and deprotection in TFA resulted in compound 139 in 70% yield, after which saponification followed by an amide coupling with tryptamine and CDI

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

• Paudler [34][50], i.e., the phenylglyoxal was condensed with the S-methylthiosemicarbazide followed by an oxidation reaction with MCPBA. Synthesis of N-substituted pent-4-ynamides N-Alkyl or N-aryl-pent-4-ynamides were prepared by amide coupling reactions between pent-4-ynoic acid and various amines in

• irradiation. Conditions: Chorobenzene, 220 °C, 1 h. Preparation of aryl-N-triazinylpentynamides. Conditions: CuI (10 mol %), Pd(PPh3)2Cl2 (5 mol %), DME, Et3N, rt, 3 h. Preparation of 3,4-dihydro-1,8-naphthridin-2(1H)-ones. Conditions: Chlorobenzene, 220 °C, 1 h. Amide coupling reactions of pent-4-ynoic acid

Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

• Felix Wojcik,
• Sinaida Lel,
• Alexander G. O’Brien,
• Peter H. Seeberger and
• Laura Hartmann

Beilstein J. Org. Chem. 2013, 9, 2395–2403, doi:10.3762/bjoc.9.276

• reaction conditions for the production of six glycosylated building blocks (Figure 1). These building blocks can then be used for the assembly of monodisperse, sequence-defined glycooligomers via fully automated standard amide coupling. Straightforward variations in the scaffold architecture, number and

Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

• M. B. Avinash,
• K. V. Sandeepa and
• T. Govindaraju

Beilstein J. Org. Chem. 2013, 9, 1565–1571, doi:10.3762/bjoc.9.178

• then subjected to amide coupling with pyrenemethylamine to obtain the triads (1–3) in good yield. UV–vis absorption spectra of 1 in dimethyl sulfoxide (DMSO) exhibit absorption bands in the region of 270–400 nm due to characteristic π–π* transitions of pyrene and NDI (Figure 2a). With the successive

A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide

• Mitsuhiro Ueda,
• Yoshitaka Uenoyama,
• Nozomi Terasoma,
• Shoko Doi,
• Shoji Kobayashi,
• Ilhyong Ryu and
• John A. Murphy

Beilstein J. Org. Chem. 2013, 9, 1340–1345, doi:10.3762/bjoc.9.151

• of this spiro structure is of continued interest for synthetic chemists. Recently, Comesse and Daïch reported the synthesis of 4,4-spirocyclic oxindole γ-lactams by tandem spirocyclization via nucleophilic halide displacement and amide coupling [4]. Shaw and co-workers reported the synthesis of 4,4

Design and synthesis of tag-free photoprobes for the identification of the molecular target for CCG-1423, a novel inhibitor of the Rho/MKL1/SRF signaling pathway

• Jessica L. Bell,
• Andrew J. Haak,
• Susan M. Wade,
• Yihan Sun,
• Richard R. Neubig and
• Scott D. Larsen

Beilstein J. Org. Chem. 2013, 9, 966–973, doi:10.3762/bjoc.9.111

• azide and acetylene, was prepared from aniline 26. Introduction of the azide was accomplished via diazotization/azidation, followed by standard amide coupling of 27 and 18 to afford final aryl azide photoprobe 28. Table 2 summaries the biological data for the four final candidate photoprobes

Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

• Rajendra Surasani,
• Dipak Kalita,
• A. V. Dhanunjaya Rao and
• K. B. Chandrasekhar

Beilstein J. Org. Chem. 2012, 8, 2004–2018, doi:10.3762/bjoc.8.227

• arylation of the heterocyclic N–H nitrogen [49][50]. To find a suitable condition for amide coupling with 7-azaindole derivatives, various biaryl/alkyl phosphine ligands, palladium catalysts, bases and reaction times, etc., were screened by using electron-deficient N-protected 4-bromo-7-azaindoles 1 as

Low-generation dendrimers with a calixarene core and based on a chiral C₂-symmetric pyrrolidine as iminosugar mimics

• Marco Marradi,
• Stefano Cicchi,
• Francesco Sansone,
• Alessandro Casnati and
• Andrea Goti

Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107

• , 80% overall yield). The amide coupling was then performed by reaction of 9 with pyrrolidine 4 using DIPEA as a base, and this afforded the branched tripyrrolidine 10 in 77% yield after column chromatography over neutral aluminium oxide. The tert-butoxycarbonyl group was then removed in the presence

Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes

• Nora L. Löw,
• Egor V. Dzyuba,
• Boris Brusilowskij,
• Lena Kaufmann,
• Elisa Franzmann,
• Wolfgang Maison,
• Emily Brandt,
• Daniel Aicher,
• Arno Wiehe and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2012, 8, 234–245, doi:10.3762/bjoc.8.24

• amide coupling with 6 yielding binding site 2 in 73% yield. Since an excess of 7 was used and the 2’/6’-positions are sterically hindered, only monoiodination in the 4’-position was observed. This synthetic pathway thus gives reasonable overall yields. It should be mentioned that the diamide moiety

Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors

• Georg Schitter,
• Elisabeth Scheucher,
• Andreas J. Steiner,
• Arnold E. Stütz,
• Martin Thonhofer,
• Chris A. Tarling,
• Stephen G. Withers,
• Jacqueline Wicki,
• Katrin Fantur,
• Eduard Paschke,
• Don J. Mahuran,
• Brigitte A. Rigat,
• Michael Tropak and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2010, 6, No. 21, doi:10.3762/bjoc.6.21

• substituent. For the synthesis of compound 16, 4-isopropylbenzoic acid was reacted with the primary amine under amide coupling conditions with O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoro-borate (TBTU) as the coupling reagent in DMF and triethylamine. Likewise, nicotinic acid under the same

The vicinal difluoro motif: The synthesis and conformation of erythro- and threo- diastereoisomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives

• David O'Hagan,
• Henry S. Rzepa,
• Martin Schüler and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2006, 2, No. 19, doi:10.1186/1860-5397-2-19

• compounds were prepared by a straightforward EDCI amide coupling between benzylamine and 2,3-difluorosuccinate 19 as shown in Scheme 10. The diasteroisomers of 22 were separated by silica gel chromatography and recrystallisation of each allowed their X-ray structures to be compared. The structure of erythro