Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

• Matthias R. Steiner,
• Max Schmallegger,
• Larissa Donner,
• Johann A. Hlina,
• Christoph Marschner,
• Judith Baumgartner and
• Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

• for the conversion of acrylamide, which is probably disturbed when the hydrogen bond donor solvent methanol is interacting with the amide group and/or the hydroxy group. Conclusion The conjugate addition of 2,4-di-tert-butyl-6-(diphenylphosphino)phenol to Michael acceptor molecules allows for a facile

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

• Lukáš Marek,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

• (Scheme 6). This means that the cleavage of the amide group that evolves aniline (pKa = 4.6) occurred smoothly after the initial thiazole ring closure (through 12a’ in Scheme 6). The addition of a thiophile (trimethyl phosphite) does not turn the reaction toward ECR and only decreases the yield of 13

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• -illustrated by Hirshfeld surfaces [41] (Figure 3e and f). The guest molecule (water or methanol) acts as an H-bond acceptor with two axial NH units (distances N···O 2.85–2.93 Å, NHO 166.4–178.0°) and as an H-bond donor for the oxygen atom of the equatorial amide group (distances O···O 2.69–2.78 Å, OHO 163.7

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

• produced a bridged cyclic 2-oxabicyclo[2.2.1]hept-5-ene D. The further hydration of intermediate D gave intermediate E, which was in turn transferred to cyclopentenyl intermediate F by the ring opening of the bridge ring. In the cyclopentenyl intermediate F, the hydroxy group and the amide group clearly

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• -hydroxyamide group (C16: δC 46.7; C27: δC 47.2) were obviously larger than the methylenes adjacent to the amide group (C20: δC 38.52; C31: δC 38.52), consistent with the reported data for avaroferrin [22], bisucaberins [18], and nocardamines [23]. However, this trend is inversed in the hydroxamic acid terminus

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

• Li Liu,
• Yue Li,
• Tiao Huang,
• Dulin Kong and
• Mingshu Wu

Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150

• has a remarkable structural feature: the phosphate moiety is located at the benzylic position as well as at the position α to an amide group, which makes it a good leaving group for the design and development of new reactions. Accordingly, diethyl (2-oxoindolin-3-yl) phosphates 2 have been used

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

• Luiz Claudio Ferreira Pimentel,
• Lucas Villas Boas Hoelz,
• Henayle Fernandes Canzian,
• Frederico Silva Castelo Branco,
• Andressa Paula de Oliveira,
• Vinicius Rangel Campos,
• Floriano Paes Silva Júnior,
• Rafael Ferreira Dantas,
• Jackson Antônio Lamounier Camargos Resende,
• Anna Claudia Cunha,
• Nubia Boechat and
• Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

• ) inherent to this type of treatment [25]. In this regard, Arioli and co-workers developed a series of derivatives (from PAPP) containing the 1,2,3-triazole nucleus in place of the amide group (present in the IMT structure) that showed inhibitory activity of recombinant Abl kinase equivalent to the drug of

• reference [26]. In this context, the intent is to replace the amide group present in IMT by the 1,2,3-triazole nucleus, similar to compound 3 described in the literature by Li and co-workers, which showed a good inhibition profile of the myelogenous leukemia K562 cell line [27]. Considering the good

• original work that led to compound 3, and, additionally, they are able to act as acceptors and donors in hydrogen bonds and thus were expected to increase the aqueous solubility of the compounds. Additionally, Kalesh and co-workers demonstrated good results with derivative 4 which contains the amide group

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• primary amide C=O stretching vibration of the amide group. The strong signals at 1558 and 1404 cm−1 are originated from amine N–H bending and scissoring –CH2– vibrations, respectively. At last, the poly(ethylene glycol) methyl ether methacrylate (PEGMEMA)-based network displays O–H stretching from 3106 cm

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

• Csilla Hargitai,
• Györgyi Koványi-Lax,
• Tamás Nagy,
• Péter Ábrányi-Balogh,
• András Dancsó,
• Gábor Tóth,
• Judit Halász,
• Angéla Pandur,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136

• ). According to the single-crystal X-ray experiments of compounds 3b, 8b, and 23a, the solid-phase structures are stabilized by a hydrogen bond between the amide NH and the carbonyl oxygen atom of the other amide group. The H–C–C–H dihedral angles between the two asymmetric centers are not far from 90° as

Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers

• Vyacheslav I. Supranovich,
• Vitalij V. Levin and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 1550–1553, doi:10.3762/bjoc.16.126

• employed in photoredox reactions to scavenge acidic byproducts [28][29], could not be employed. Silane 1 is easily destroyed by bases (even by the amide group [30]) followed by the rapid addition of difluorocarbene to silyl enol ethers [19][20]. Disappointingly, we were unable to isolate ketone 3a using

The McKenna reaction – avoiding side reactions in phosphonate deprotection

• Katarzyna Justyna,
• Joanna Małolepsza,
• Damian Kusy,
• Waldemar Maniukiewicz and
• Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 1436–1446, doi:10.3762/bjoc.16.119

• problem. Section 1: Formation of oxazoles from propargylamides One of the most intriguing side reactions was observed when compounds comprising a propargyl amide group were treated with BTMS. Besides the products of addition of HBr, we observed the formation of oxazole. In order to study this process, we

Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position

• Yongsu Li,
• Bendu Pan,
• Xuefeng He,
• Wang Xia,
• Yaqi Zhang,
• Hao Liang,
• Chitreddy V. Subba Reddy,
• Rihui Cao and
• Liqin Qiu

Beilstein J. Org. Chem. 2020, 16, 966–973, doi:10.3762/bjoc.16.85

• hindrance of the 4-substituted boronic acid. Next, in order to confirm our speculation, the amide group of the aryl bromide was replaced with other functional groups, as shown in Scheme 2. When the amide group was changed into an amine, coupling product 5a was obtained quantitatively but without any

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• 22 upon coordination with the carbonyl oxygen atom of the amide group. The complex 22 then coordinated to the acrylate product 23, which rearranged to 24, and the β-hydride elimination of 24 yielded the desired olefinated product 21. C–H olefination of phenolic ethers: Based on Ackermann and co

The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds

• Itamar L. Gonçalves,
• Rafaela R. da Rosa,
• Vera L. Eifler-Lima and
• Aloir A. Merlo

Beilstein J. Org. Chem. 2020, 16, 175–184, doi:10.3762/bjoc.16.20

• behavior displayed SmA mesophase. A similar liquid crystal behavior can be seen in amides 19 and 21 where the isomers differ only in the relative orientation of the isoxazoline ring to the amide group, while the amide group in 19 can resonate to the nitrogen atom in the isoxazoline ring, 21 does not. All

Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol

• María C. Mollo,
• Natalia B. Kilimciler,
• Juan A. Bisceglia and
• Liliana R. Orelli

Beilstein J. Org. Chem. 2020, 16, 32–38, doi:10.3762/bjoc.16.5

• excess, (LR/substrate 2.5:1, toluene, reflux) the reaction was chemoselective toward the amide group, and compound 2a was obtained in high yield (93%), although the unreacted LR complicated the isolation and purification of the product. Lowering the molar ratio of the starting materials to strictly

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• using a secondary amide as directing group (Scheme 1C) [32][48]. In these protocols, the amide group plays a dual behavior of directing group and reaction center, as it participates in the final ring-closing reductive elimination. Herein, we report the synthesis of a new class of tetrazolo-isoquinolone

• evaluate the effect of the substituent in the phenyl ring. Interestingly, the presence of substituents in the ortho-position of the amide group (acting as a directing group) decreased the yields, with substrates bearing substituents Me, Br and Cl leading to moderate yields of compounds 4b, 4c, and 4d

• , while a OMe substituent in this position no product 4e was obtained. On the other hand, no significant effect was observed when the substituents were placed in the meta- or para-position (4f–m) of the amide group. It must be noted that for substrates bearing a halogen (1k–m) in the meta-position of the

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

• Xiaowei Li,
• Xiaolin Shi,
• Xiangqian Li and
• Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

• -selective fluorination of α-bromocarbonyl compounds using a copper/CsF catalyst system (Scheme 32). Tertiary alkyl fluorides could be generated by this fluorination through the assistance of an amide group. From the results, the catalytic cycle of this reaction includes: 1) copper salt induced generation of

• the alkyl radical species B from substrate A and 2) fluorination of the alkyl radical species B with CuF2, which is in situ-generated from the reaction of CuXBr and CsF with the aid of an amide group, gives the desired product and recyclable CuF. Csp2–H bond formation catalyzed by Cu catalysts: In

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

• Christoph W. Grathwol,
• Nathalie Wössner,
• Sören Swyter,
• Adam C. Smith,
• Enrico Tapavicza,
• Robert K. Hofstetter,
• Anja Bodtke,
• Manfred Jung and
• Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

• selective Sirt1 inhibitor, passed phase II clinical trials as a disease-modifying therapeutic for Huntington’s disease (HD) and was acquainted by AOP Orphan Pharmaceuticals AG for phase III trials in 2017 [9][10]. Its structure comprises a carboxamide moiety, which mimics the amide group of the endogenous

Tautomerism as primary signaling mechanism in metal sensing: the case of amide group

• Vera Deneva,
• Georgi Dobrikov,
• Aurelien Crochet,
• Daniela Nedeltcheva,
• Katharina M. Fromm and
• Liudmil Antonov

Beilstein J. Org. Chem. 2019, 15, 1898–1906, doi:10.3762/bjoc.15.185

• , Switzerland 10.3762/bjoc.15.185 Abstract The concept for sensing systems using the tautomerism as elementary signaling process has been further developed by synthesizing a ligand containing 4-(phenyldiazenyl)naphthalene-1-ol as a tautomeric block and an amide group as metal capturing antenna. Although it has

• been expected that the intramolecular hydrogen bonding (between the tautomeric hydroxy group and the nitrogen atom from the amide group) could stabilize the pure enol form in some solvents, the keto tautomer is also observed. This is a result from the formation of intramolecular associates in some

• solvents. Strong bathochromic and hyperchromic effects in the visible spectra accompany the 1:1 formation of complexes with some alkaline earth metal ions. Keywords: amide group; azo dye; molecular sensor; sidearm; tautomerism; Introduction The design of new organic sensing systems is an undividable part

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

• Leon Buschbeck,
• Aleksandra Markovic,
• Gunther Wittstock and
• Jens Christoffers

Beilstein J. Org. Chem. 2019, 15, 981–991, doi:10.3762/bjoc.15.96

• the first title compound 3 in 71% yield. Due to the electron-withdrawing amide group, the chromophore is relatively electron deficient (absorption at 420 nm and emission at 495 nm). In order to achieve a bathochromic shift of absorption and emission bands, the DAT and ALA moieties should be

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

• glycosylation (Figure 3). This intermediate is subsequently approached by Nam from the less hindered side. Subsequently, Franchetti et al. [30] modified the above TMSOTf-protocol by introducing the preliminary silylation of the amide group of Nam, a procedure based on the chemistry developed by Vorbrüggen [24

Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

• Pedro N. Batalha,
• Luana da S. M. Forezi,
• Maria Clara R. Freitas,
• Nathalia M. de C. Tolentino,
• Ednilsom Orestes,
• José Walkimar de M. Carneiro,
• Fernanda da C. S. Boechat and
• Maria Cecília B. V. de Souza

Beilstein J. Org. Chem. 2019, 15, 388–400, doi:10.3762/bjoc.15.35

• regioselective manner, without the formation of any byproduct derived from the N-alkylation of the amide group. Structural characterization Table 1 gives the nuclear magnetic resonance spectroscopic data that allowed to confirm the structures of substances 5 and 7, and thus also confirmed the regioselectivity of

• HMBC spectra. In the COSY spectrum of 7, the correlations between the hydrogen of the amide group (CONH) and of the benzylic hydrogens (CONHCH2Ph) confirm again the occurrence of the alkylation in the nitrogen of the oxoquinoline nucleus (Figure 4). From the HMBC spectrum of 7 it was observed that H-2

• structure that the intramolecular hydrogen bond between the hydrogen of the amide group, CON–H, and the carbonyl oxygen (C-4), promotes coplanarity between the oxoquinoline nucleus and the CONH moiety of this amide group connected to C-3, as expected. An additional crystallographic description and the full

Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes

• Guillaume Ernouf,
• Jean-Louis Brayer,
• Christophe Meyer and
• Janine Cossy

Beilstein J. Org. Chem. 2019, 15, 333–350, doi:10.3762/bjoc.15.29

• -acylamino)cyclopropanes] possessing a single substituent at C2, it is possible to rely either on the steric hindrance or on the coordinating ability of the amide group. Thus, the hydrogenation of trifluoroacetamide 51 catalyzed by Pd/C afforded N-trifluoroacetylaminocyclopropane 55 as the major diastereomer

Synthesis of 3-aminocoumarin-N-benzylpyridinium conjugates with nanomolar inhibitory activity against acetylcholinesterase

• Nisachon Khunnawutmanotham,
• Cherdchai Laongthipparos,
• Patchreenart Saparpakorn,
• Nitirat Chimnoi and
• Supanna Techasakul

Beilstein J. Org. Chem. 2018, 14, 2545–2552, doi:10.3762/bjoc.14.231

• the amide group and dimethoxy substituents on the chromene ring to the amino acid residues Tyr72, Tyr124, Trp286, and Tyr341 in the PAS; and (5) the hydrogen atoms of phenyl ring to Glu202 and a methoxy group to Ser293. Moreover, C–H–π and π–π interactions were found for compound 9h. The C–H–π

• and of the amide group to Phe338 in the CAS and between the nitrogen atom of the amide group to Tyr124 in the PAS were the key interactions of the synthesized 3-aminocoumarin-N-benzylpyridinium conjugates in the binding pocket of AChE. Conclusion A series of 3-amino-6,7-dimethoxycoumarins conjugated