Base-promoted cascade recyclization of allomaltol derivatives containing an amide fragment into substituted 3-(1-hydroxyethylidene)tetronic acids

• Andrey N. Komogortsev,
• Constantine V. Milyutin and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 2585–2591, doi:10.3762/bjoc.20.217

• fragment in the side chain were investigated. It was shown that the studied process leads to substituted tetronic acids bearing a pyrrolidinone moiety. The application of 1,1′-carbonyldiimidazole and DBU is necessary for implementation of the considered reaction. Based on the performed research a general

• ; 1,1′-carbonyldiimidazole; 3-hydroxypyran-4-ones; tetronic acid; Introduction 3-Hydroxypyran-4-one derivatives are an important class of heterocyclic compounds widely represented in various naturally occurring sources [1][2][3][4]. Products of this type demonstrate a broad range of biological activity

• 3-acetyltetronic acids 2 under action of 1,1-carbonyldiimidazole (CDI) [32] (Scheme 1A). We assumed that the aforementioned synthetic strategy can be extended to other 3-hydroxypyran-4-one derivatives with a nitrogen functional group in the side chain. Ongoing our research in this area in the

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

• Olfa Mhasni,
• Jalloul Bouajila and
• Farhat Rezgui

Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93

• derivatives in Et3N/THF mixtures [20] (Scheme 1, reaction 1, i) and acetates in THF/water [21] (Scheme 1, reaction 1, ii), or MBH alcohols in the presence of CDI (1,1’-carbonyldiimidazole) in acetonitrile (Scheme 1, reaction 1, iii) [22]. In the last case, as the hydroxy moiety is not a good leaving group

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky,
• Mikhail E. Minyaev and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2023, 19, 778–788, doi:10.3762/bjoc.19.58

• could be achieved by using suitable dehydrating agents (TsOH/toluene, Ac2O/MeCN, SOCl2/toluene, CDI/MeCN, POCl3/toluene). Gratifyingly, it was shown that the application of 1,1-carbonyldiimidazole (CDI) in acetonitrile allows to convert compound 11g into the polyaromatic product 12a in 94% yield (see

From amines to (form)amides: a simple and successful mechanochemical approach

• Federico Casti,
• Rita Mocci and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126

• -Ts-Im), a cheap and commercially available reagent directly prepared from p-toluensulfonic acid by reaction with 1,1′-carbonyldiimidazole (CDI). The compound proved very effective for dehydrating oximes under mechanochemical acidic Beckmann conditions [44]. Moreover, it represents a suitable and

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

• Attila Márió Remete,
• Tamás T. Novák,
• Melinda Nonn,
• Matti Haukka,
• Ferenc Fülöp and
• Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

• trans-4-cyclohexene-1,2-diamine dihydrochloride and 1,1’-carbonyldiimidazole (CDI), through a slightly modified literature protocol [36], the desired product was isolated in only 10% yield (Scheme 7). Increasing the reaction temperature considerably decreased the product purity. With the low yield in

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• aprotic liquids (e.g., N,N-dimethylformamide or dimethyl sulfoxide), which affect the final result, especially for potential biomedical applications. This article describes a new, green synthetic pathway through mechanochemistry, in particular via ball milling and using 1,1-carbonyldiimidazole as the

• afforded a biodegradable polymer, displaying the same characteristics as cyclodextrin-based polymers synthesized in a solvent-based approach. The CD-based carbonate NSs were synthesized using an active carbonyl compound as a crosslinker, 1,1-carbonyldiimidazole, leading to an insoluble crosslinked polymer

• goal of this work was to obtain cyclodextrin nanosponges via a ball-milling-driven synthesis, having the same physicochemical characteristics as the material synthesized through the solvent-based approach. Among the various types of cyclodextrin nanosponges, we chose carbonate NS, synthesized with 1,1

Microwave-assisted synthesis of biologically relevant steroidal 17-exo-pyrazol-5'-ones from a norpregnene precursor by a side-chain elongation/heterocyclization sequence

• Gergő Mótyán,
• László Mérai,
• Márton Attila Kiss,
• Zsuzsanna Schelz,
• Izabella Sinka,
• István Zupkó and
• Éva Frank

Beilstein J. Org. Chem. 2018, 14, 2589–2596, doi:10.3762/bjoc.14.236

• multistep sequence (Scheme 1). First compound 1 was converted to the 17β-carboxylic acid 2b by the bromoform reaction and subsequent acetylation according to well-known literature procedures [21][22][23]. After the activation of 2b with 1,1′-carbonyldiimidazole (CDI) as coupling reagent in THF, the

Functionalization of graphene: does the organic chemistry matter?

• Artur Kasprzak,
• Agnieszka Zuchowska and
• Magdalena Poplawska

Beilstein J. Org. Chem. 2018, 14, 2018–2026, doi:10.3762/bjoc.14.177

• mediated by the 1,1’-carbonyldiimidazole, which acts as the coupling reagent. The mechanism of this method is presented in Figure 6. The basic principles of this process are the same as for those of carbodiimide-mediated protocol (a reaction between activated ester and a nucleophile). As presented in

• hydrohalide using an acid–base reaction with the tertiary amine. Mechanism of amidation/esterification-type reactions with the GO/RGO using 1,1’-carbonyldiimidazole: (a) activation of the carboxyl group with 1,1’-carbonyldiimidazole, (b) amidation/esterification-type reaction with the desired nucleophile, (c

A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic

• Marcus Baumann,
• Ian R. Baxendale and
• Fabien Deplante

Beilstein J. Org. Chem. 2017, 13, 2549–2560, doi:10.3762/bjoc.13.251

• the desired product 8 through the action of a reactive carbonyl donor such as CDI (1,1′-carbonyldiimidazole) or triphosgene (bis(trichloromethyl)carbonate). This synthetic strategy presented various advantages as it relies on readily available substrates and reagents, creates small amounts of non

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• 65–81% of trans-esterified product (Scheme 21). Differently substituted benzene rings including hetero-aromatics were also well tolerated under the similar condition. Colacino and co-workers reported the preparation of carbamates by using 1,1’-carbonyldiimidazole (CDI) and in presence of either

Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

• Andrea Mascitti,
• Massimiliano Lupacchini,
• Ruben Guerra,
• Ilya Taydakov,
• Lucia Tonucci,
• Nicola d’Alessandro,
• Frederic Lamaty,
• Jean Martinez and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 19–25, doi:10.3762/bjoc.13.3

• agents. In general, cleaner reaction profiles were observed in the presence of PEGs, compared to dry-grinding procedures. Keywords: ball-milling; 1,1’-carbonyldiimidazole (CDI); hydantoins; mechanochemistry; liquid-assisted grinding (LAG); poly(ethylene) glycols (PEGs); Introduction Poly(ethylene

Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes

• Luke J. O’Driscoll,
• Sissel S. Andersen,
• Marta V. Solano,
• Dan Bendixen,
• Morten Jensen,
• Troels Duedal,
• Jess Lycoops,
• Cornelia van der Pol,
• Rebecca E. Sørensen,
• Karina R. Larsen,
• Kenneth Myntman,
• Christian Henriksen,
• Stinne W. Hansen and
• Jan O. Jeppesen

Beilstein J. Org. Chem. 2015, 11, 1112–1122, doi:10.3762/bjoc.11.125

• . The reduction of the thiocyanate moieties with LiAlH4 afforded the air-sensitive intermediate 18 (not characterised), which was treated with 1,1’-carbonyldiimidazole to afford 7, in 83% yield over the two steps. Preparation of functionalised MPTTFs and BPTTFs Coupling reactions Pyrrole-annelated TTF

Synthesis of 2,6-disubstituted tetrahydroazulene derivatives

• Zakir Hussain,
• Henning Hopf,
• Khurshid Ayub and
• S. Holger Eichhorn

Beilstein J. Org. Chem. 2012, 8, 693–698, doi:10.3762/bjoc.8.77

• reduced under Birch conditions [15] to 4,7-dihydro-2-indancarboxylic acid (2) as the kinetically controlled product. In order to carry out carbene additions to the obtained 1,4-cyclohexadiene system, esterification [16] of 2 was carried out in a one-pot procedure in DMF at 40 °C with 1,1

• '-carbonyldiimidazole, tert-butyl alcohol and DBU to afford ester 3 in quantitative yield. The ester 3 was then subjected to carbene addition by treatment with ethyl diazoacetate in the presence of a copper catalyst [17] in THF under reflux. The carbene adduct 4 was obtained as the major product, as a colorless oil in

Approaches towards the synthesis of 5-aminopyrazoles

• Ranjana Aggarwal,
• Vinod Kumar,
• Rajiv Kumar and
• Shiv P. Singh

Beilstein J. Org. Chem. 2011, 7, 179–197, doi:10.3762/bjoc.7.25

• solid-phase synthesis of 5-aminopyrazoles 42 which were used as precursors for the preparation of pyrazolo[5,1-d][1,2,3,5]tetrazine-4(3H)-ones 43. Resin 39, obtained from Wang resin 38 and a 5-10 fold excess of 1,1′-carbonyldiimidazole (CDI), was treated with hydrazine hydrate in THF at room temperature

Synthetic incorporation of Nile Blue into DNA using 2′-deoxyriboside substitutes: Representative comparison of (R)- and (S)-aminopropanediol as an acyclic linker

• Daniel Lachmann,
• Sina Berndl,
• Otto S. Wolfbeis and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2010, 6, No. 13, doi:10.3762/bjoc.6.13

• we have shown with indole [32] and thiazole orange [33][34]. DMT-protected (R)-3-amino-1,2-propanediol 1 as a precursor was synthesized according to literature [29][43]. The hydroxy function of commercially available 2-propyn-1-ol was converted into an activated ester by 1,1′-carbonyldiimidazole and

• counterparts Y = A, T, C, G; a) 2-propyn-1-ol, 1,1′-carbonyldiimidazole, DMF, r.t., 27 h; 44%; b) 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite, EtN(iPr)2, CH2Cl2, r.t., 3 h. Melting temperatures (Tm) and quantum yields (ΦF) of duplex sets DNA1Y and DNA2Y bearing the R-configured linker in comparison to

• 3 fluorimeter in spectral steps of 1 nm and an integration time of 0.2 s. All spectra were recorded with an excitation and emission bandpass of 2 nm and are corrected for Raman emission from the buffer solution. Synthesis of 2. 2-Propyn-1-ol (40 µL, 700  µmol) was dissolved in DMF (5 mL). 1,1