Synthesis of new tricyclic 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepine derivatives by [3⁺ + 2]-cycloaddition/rearrangement reactions

• Lin-bo Luan,
• Zi-jie Song,
• Zhi-ming Li and
• Quan-rui Wang

Beilstein J. Org. Chem. 2018, 14, 1826–1833, doi:10.3762/bjoc.14.155

• of nitriles, the strategy was also probed with aromatic nitriles 9 that were reacted with 8 under the same reaction conditions. The nucleophilicity of the N atom in aromatic nitriles should be lower than that of aliphatic ones owing to the conjugation of the triple bond with the benzene ring. To our

• proceeded as expected under the usual reaction conditions and the desired products 13 were obtained after quenching with H2O at 0 °C. As can be seen from Scheme 4, both aliphatic and aromatic nitriles worked similarly. In light of the experimental achievements and preceding theoretical work, we rationalized

Cobalt-catalyzed C–H cyanations: Insights into the reaction mechanism and the role of London dispersion

• Eric Detmar,
• Valentin Müller,
• Daniel Zell,
• Lutz Ackermann and
• Martin Breugst

Beilstein J. Org. Chem. 2018, 14, 1537–1545, doi:10.3762/bjoc.14.130

• Abstract Carboxylate-assisted cobalt(III)-catalyzed C–H cyanations are highly efficient processes for the synthesis of (hetero)aromatic nitriles. We have now analyzed the cyanation of differently substituted 2-phenylpyridines in detail computationally by density functional theory and also experimentally

Novel approach to hydroxy-group-containing porous organic polymers from bisphenol A

• Tao Wang,
• Yan-Chao Zhao,
• Li-Min Zhang,
• Yi Cui,
• Chang-Shan Zhang and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 2131–2137, doi:10.3762/bjoc.13.211

• organic polymers (POPs) have been reported via Sonogashira–Hagihara coupling reaction [16], Suzuki–Miyaura chemistry [17], Yamato reaction [18], and self condensation of aromatic nitriles[19]. Although these methods can be used to construct POPs with high specific surface area values, these reactions are

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• proton source (Scheme 1). Using Na/NH3 or Li/EtNH2 solutions, Arapakos obtained the best yields for the decyanation of phenyl-substituted acetonitriles, tertiary alkyl, and aromatic nitriles. However, primary and secondary nitriles also led to the reduction to the amine [10][16]. This drawback can be

• bond cleavage catalyzed by iron complexes of a few primary alkyl cyanides and aryl cyanides in the presence of Et3SiH [100][101]. Decyanated species were formed together with silyl cyanide. Both aliphatic and aromatic nitriles were successfully reduced (Scheme 16) but an electron-withdrawing, bulky or

One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

• Roman Yu. Peshkov,
• Elena V. Panteleeva,
• Wang Chunyan,
• Evgeny V. Tretyakov and
• Vitalij D. Shteingarts

Beilstein J. Org. Chem. 2016, 12, 1577–1584, doi:10.3762/bjoc.12.153

• yield in the reaction with acetal 6f is probably due to the latter’s lower reactivity compared to other alkylating reagents, what was indicated by increased yield of dicyanobiphenyl 4 (14% vs 5% formed in reactions with 6b–e). To demonstrate the effects of varying the aromatic moiety, a set of aromatic

• nitriles containing substituents of different natures and positions were used in the reaction (Table 2). We chose the nitriles that had earlier effectively underwent a cross-coupling with dianion 12− [24][25], in particular, 2- and 3-methyl (2b,c), 2- and 3-methoxy- (2d,e), and 2-fluorobenzonitrile (2f

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

• Madhuri Vangala and
• Ganesh P. Shinde

Beilstein J. Org. Chem. 2015, 11, 2289–2296, doi:10.3762/bjoc.11.249

• products. With this optimization, we began to explore the scope of the reaction by employing various aliphatic and aromatic nitriles bearing electron-donating and electron-withdrawing substituents. Accordingly, compound 5a was treated with allyl cyanide (Table 1, entry 4) to get 9a in 53% yield in a

• . Attention then was turned to check the feasibility of the reaction with different substituted, aromatic nitriles. In this respect, electron-rich aromatic nitriles, such as 3-methyl, 4-methyl, 4-methoxybenzonitrile (Table 1, entries 5–7) and 1-naphthonitrile (Table 1, entry 9), reacted with 3a and 5a

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

A Lewis acid-promoted Pinner reaction

• Dominik Pfaff,
• Gregor Nemecek and
• Joachim Podlech

Beilstein J. Org. Chem. 2013, 9, 1572–1577, doi:10.3762/bjoc.9.179

• identified as an imidate hydrochloride (Scheme 1). Best results in the Pinner reaction are obtained with primary or secondary alcohols and aliphatic or aromatic nitriles. A plausible mechanism (Scheme 2) starts with a protonation of the nitrile by the strong acid hydrogen chloride leading to a highly

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

• Maurizio Fagnoni,
• Stefano Protti,
• Davide Ravelli and
• Angelo Albini

Beilstein J. Org. Chem. 2013, 9, 800–808, doi:10.3762/bjoc.9.91

• Maurizio Fagnoni Stefano Protti Davide Ravelli Angelo Albini PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy 10.3762/bjoc.9.91 Abstract Steady-state irradiation in neat acetonitrile of some aromatic nitriles, imides and esters (10−5–10−3 M

• intermediates. Keywords: aromatic nitriles; persistent radical anion; photochemical activation; photoinduced electron transfer (PET); photooxidant; reactive intermediates; Introduction Redox reactions between organic molecules have a limited scope because of the rarely matched redox potential. On the other

• reduced and an oxidized product is formed. As an example, the largely positive reduction potential of aromatic nitriles [5][8][9] and cyanophthalimides [10] in the singlet excited state or of aromatic esters in the triplet state [5][11] makes PET a common occurrence upon irradiation of such substrates in

Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles

• Peter Wipf and
• Marija D. Manojlovic

Beilstein J. Org. Chem. 2011, 7, 824–830, doi:10.3762/bjoc.7.94

• regioisomer. Other aliphatic nitriles were also good substrates for this reaction; however, N-aluminoimines obtained from aromatic nitriles were unreactive towards allylzirconocenes, and the desired product was not detected from these substrates (Table 1). We also investigated the one-pot hydrozirconation of

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• step in high yield by the reaction of benzonitrile (or other aromatic nitriles) with succinic acid diesters. Numerous DPP derivatives have since been synthesized, their colours ranging from orange yellow via red to purple. Many DPP derivatives exhibit a high photostability in the solid state, weather