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Search for "carboxamide" in Full Text gives 106 result(s) in Beilstein Journal of Organic Chemistry.

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

Graphical Abstract
  • -carboxamide-1,4-benzodiazepin-5-ones when enantiopure (S)-(−)-α-methylbenzylamine and arylglyoxals were used. Thus, a reversal of diastereoselectivity was observed depending on the cyclization methodology employed, the reduction of a nitro group or the Staudinger/aza-Wittig on azide derivatives. This
  • using the Gewald multicomponent reaction and the best candidate synthesized. Development of 1,5-benzodiazepines via Ugi/deprotection/cyclization (UDC) approach by Xu et al. [59]. Synthesis of polysubstituted 1,4-benzodiazepin-3-ones using UDC strategy. Synthetic procedure to obtain 3-carboxamide-1,4
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Published 03 Dec 2024

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

  • Dmitriy Yu. Vandyshev,
  • Daria A. Mangusheva,
  • Khidmet S. Shikhaliev,
  • Kirill A. Scherbakov,
  • Oleg N. Burov,
  • Alexander D. Zagrebaev,
  • Tatiana N. Khmelevskaya,
  • Alexey S. Trenin and
  • Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

Graphical Abstract
  • -aminoimidazole (1). Results of MEP calculations for the reaction of N-phenylithaconimide (3a) with 2-aminoimidazole (1). Screening of reaction conditions for the preparation of 7-oxo-N-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-5-carboxamide (4a). Yields of the products 4 and 5. Characterization of ligand
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Published 05 Nov 2024

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

  • Anthony J. Burke and
  • Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

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  • a new family of isatin-based α-acetamide carboxamide oxindole hybrids using the versatile Ugi four-component reaction [18]. Sixteen hybrids were prepared by reacting 5-amino-1-benzyl-3,3-dimethoxyindolin-2-one, benzyl isocyanide, carboxylic acids, and aldehyde/ketone derivatives, catalyzed by ZnF2
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Published 28 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Graphical Abstract
  • , enabling further functionalization. The proposed mechanism involves radical–radical cross-coupling. The indole 1H-carboxamide generates a nitrogen-centered radical during anodic oxidation in the presence of a base, while the 1,3-dimethylindole derivative forms an indole radical cation. The radical–radical
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Published 09 Oct 2024

Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

  • Yuri A. Sidunets,
  • Valeriya G. Melekhina and
  • Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

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  • Federation 10.3762/bjoc.20.200 Abstract A straightforward protocol for the synthesis of a previously unknown [1,2,5]oxadiazolo[3,4-d][1,2,3]triazin-7(6H)-one heterocyclic system was developed. The described approach is based on tandem diazotization/azo coupling reactions of (1,2,5-oxadiazolyl)carboxamide
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Published 16 Sep 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

Graphical Abstract
  • pyrazole starting materials from isonitriles 158, dialkyl acetylenedicarboxylate 147, and hydrazine carboxamide 159. The addition of the isonitrile to the Michael system yields a nitrilium-vinyl anion zwitterion 161, that is protonated by the hydrazine carboxamide, which undergoes addition to furnish the
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Published 16 Aug 2024

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
  • amines 136a–e and 138 showed better 17β-HSD3 inhibition at 0.1 µM than the secondary ones 134a–e, with some of them presenting better inhibition values than the reference compounds (RM-532-105 and D-5-2). However, only morpholinones 138 that bear sulfonamide and carboxamide groups did not exhibit
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Published 24 Jul 2024

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

  • Carolina S. Marques,
  • Aday González-Bakker and
  • José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

Graphical Abstract
  • , we highlight the reputation of this reaction approach to access number and scaffold diversity of a library of isatin-based α-acetamide carboxamide oxindole hybrids, promising anticancer agents, in a mild and fast sustainable reaction process. The library was tested against six human solid tumor cell
  • processes, a second family of α-acetamide carboxamide oxindole derivatives 5 was obtained using the previously optimized Ugi4CR approach [16] (Scheme 2 and Figure 2). Taking into account the preliminary SAR studies reported for the first family of Ugi-derived isatin-peptoids, the second family was obtained
  • -acetamide carboxamide oxindole hybrids 5 was obtained in moderate yields (26–63%), at room temperature, in short time (2 hours), proving the efficiency and the generality of this methodology. Aliphatic (2a, 2c and 2m), aromatic (2d, 2f, 2g, 2k and 2l), heterocyclic (2e, 2h, 2i, 2n and 2o), alkyne 2b and
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Published 27 May 2024

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

  • Jens Frackenpohl,
  • David M. Barber,
  • Guido Bojack,
  • Birgit Bollenbach-Wahl,
  • Ralf Braun,
  • Rahel Getachew,
  • Sabine Hohmann,
  • Kwang-Yoon Ko,
  • Karoline Kurowski,
  • Bernd Laber,
  • Rebecca L. Mattison,
  • Thomas Müller,
  • Anna M. Reingruber,
  • Dirk Schmutzler and
  • Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

Graphical Abstract
  • -ynylcarbamoyl)-1,3-dioxolane-2-carboxamide [3] and FAM azide, 5-isomer (Broadpharm BP-22544, San Diego, CA) by click chemistry [29] and was purified by flash column chromatography on silica gel. Preemergence efficacy of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine-based FAT inhibitors 7b, 7c, and 13b as well as
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Published 01 Mar 2024

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

  • Yordanka Mollova-Sapundzhieva,
  • Plamen Angelov,
  • Danail Georgiev and
  • Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

Graphical Abstract
  • key o-nitrobenzoyl intermediates 3 in a reaction with o-nitrobenzoyl chloride (Scheme 1, conditions ii). The acylation of 2 to 3 proceeded with variable yields, depending on the substituents R1 and R2. Derivatives 2 with a primary carboxamide group (R2 = H) gave generally lower and poorly reproducible
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Published 23 Nov 2023

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

Graphical Abstract
  • Lewis base organocatalysts (Scheme 56) [88]. In this procedure, the cyclized products were obtained via the activation of the sulfur electrophile by a Lewis base to generate the thiiranium ion intermediate from the β,γ-unsaturated sulfonyl carboxamide. The attack of the sulfonamide nitrogen atom on this
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Published 27 Sep 2023

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

  • Till Steinmetz,
  • Blaise Kimbadi Lombe and
  • Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

Graphical Abstract
  • formation of the terminal carboxamide in 6 might be due to a spontaneous C–N bond cleavage, which occurs in 1’’ prior to the cyclization, consistent with a mechanism recently proposed in photoxenobactin biosynthesis [34]. Despite the widespread occurrence of siderophores featuring a phenolic moiety with a
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Published 23 Jun 2023

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

  • Haritha Sindhe,
  • Malladi Mounika Reddy,
  • Karthikeyan Rajkumar,
  • Akshay Kamble,
  • Amardeep Singh,
  • Anand Kumar and
  • Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

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Published 12 Jun 2023

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

  • Alena V. Dmitrieva,
  • Oleg A. Levitskiy,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

Graphical Abstract
  • )-1-benzylpyrrolidine-2-carboxamide) and its Ni(II)–Schiff base complexes formed of glycine, serine, and dehydroalanine are reported. A bulky tert-butyl substituent in the phenylene fragment precludes unwanted oxidative dimerization of the Schiff base complex, making it suitable for targeted
  • )-benzylproline lead to (S)-N-(2-benzoyl-5-tert-butylphenyl)-1-benzylpyrrolidine-2-carboxamide (L7) in 73% yield with 96% ee (see Supporting Information File 1). The self-assembly of the three components L7, Ni(NO3)2, and glycine gave the corresponding (GlyNi)L7 complex which was isolated in 66% yield and fully
  • (S)-N-benzylproline-derived ligand (S)-N-(2-benzoyl-5-tert-butylphenyl)-1-benzylpyrrolidine-2-carboxamide and its Ni(II)–Schiff base complexes formed of glycine, serine, and dehydroalanine are reported. The bulky tert-butyl substituent inserted in the phenylene fragment of the ligand allowed to solve
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Published 27 Apr 2023

An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

  • Shubham Sharma,
  • Dharmender Singh,
  • Sunit Kumar,
  • Vaishali,
  • Rahul Jamra,
  • Naveen Banyal,
  • Deepika,
  • Chandi C. Malakar and
  • Virender Singh

Beilstein J. Org. Chem. 2023, 19, 231–244, doi:10.3762/bjoc.19.22

Graphical Abstract
  • product was the desired product, 5-(4-fluorophenyl)-1-phenyl-N-(pyridin-2-yl)-1H-pyrazole-3-carboxamide (1F), as analyzed by spectroscopic data. Next, we screened other organic solvents including DMF, CH3CN, THF, and MeOH to improve the yield of the desired product 1F, but only a slight improvement in the
  • . Using this method, 3-(4-chlorophenyl)-1-phenyl-N-(pyridin-2-yl)-1H-pyrazole-5-carboxamide (10F) was produced in good yield (62%), while 9F was generated in low yield (36%) as depicted in Scheme 8. Based on the current experimental observations and literature reports [62][83] a plausible mechanistic
  • %; Rf 0.68, (hexane/EtOAc 70:30, v/v)). Typical procedure for the synthesis of compounds 1F, 1G, 4F, 9F, and 10F as exemplified for 5-(4-fluorophenyl)-1-phenyl-N-(pyridin-2-yl)-1H-pyrazole-3-carboxamide (1F): To a stirred solution of compound 1 (0.10 g, 0.37 mmol) and 2-aminopyridine (F, 0.04 g, 0.42
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Published 02 Mar 2023

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

  • Elenilson F. da Silva,
  • Krist Helen Antunes Fernandes,
  • Denise Diedrich,
  • Jessica Gotardi,
  • Marcia Silvana Freire Franco,
  • Carlos Henrique Tomich de Paula da Silva,
  • Ana Paula Duarte de Souza and
  • Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

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  • , University of São Paulo, Ribeirão Preto, SP 14040-020, Brazil 10.3762/bjoc.18.161 Abstract Respiratory syncytial virus (RSV) is a major cause of acute lower respiratory tract infections in infants. Currently, ribavirin, a nucleoside analog containing a 1,2,4-triazole-3-carboxamide moiety, is a first-line
  • with COVID-19 precautions; however, they state that less RSV cases now could reduce immunity and they fear there will be a rebound in infections after the pandemic [4][5][6][7]. As a therapeutic resource, ribavirin, a nucleoside analog prodrug containing a 1,2,4-triazole-3-carboxamide moiety (RBV
  • -triazole ring introduced by click chemistry in order to mimic the 1,2,4-triazole-3-carboxamide structure of RBV. This strategy was based on the bioisosteric relationship between both rings established in several papers [32][33][34]. Studies have made modifications at the C-3 and C-28 positions of
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Published 09 Nov 2022

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH4/I2 system

  • Lin Chen,
  • Xuan Zhou,
  • Zhiyong Chen,
  • Changxu Wang,
  • Shunjie Wang and
  • Hanbing Teng

Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104

Graphical Abstract
  • materials including amines, carboxylic acids and isocyanates under mild and safe reaction conditions. Results and Discussion Initially, N-phenethyl-1H-imidazole-1-carboxamide (1b) was chosen as a model substrate to react with 3.0 equiv of NaBH4 and 1.0 equiv of I2 in THF at reflux temperature, as expected
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Published 17 Aug 2022

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

Graphical Abstract
  • multifunctionalized carboxamide-bridged dicyclopentenes in moderate to good yields and with high diastereoselectivity. Keywords: carboxamide; cycloaddition; cyclopentene; electron-deficient alkyne; phenacylmalononitrile; Introduction Phenacylmalononitrile is one of the privileged functionalized compounds [1][2][3
  • base-promoted reactions between phenacylmalononitriles and dialkyl but-2-ynedioates. Here we wish to report the selective synthesis of cyclopent-1-ene-1,2-dicarboxylates and complex carboxamide-bridged dicyclopentene derivatives in good yields and with high diastereoselectivity (reaction 5 in Scheme 1
  • ). From the two figures, it can be seen that a cyclopentadiene moiety is connected to a cyclopent-1-ene moiety by a carboxamide unit (CONH). Although one hydroxy group is eliminated to give the cyclopentadiene ring, another hydroxy group is still present in the cyclopent-1-ene ring. Additionally, in the
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Published 08 Aug 2022

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

Graphical Abstract
  • reaction of 2-imino-2H-chromene-3-carboxamide (228) and diethyl phosphite at 80–90 °C under the catalysis of boron trifluoride, afforded 4-amino-1-ethoxy-9b-hydrochromeno[4,3-c][1,2]azaphosphol-3(2H)-one 1-oxide (229) in 40% yield through the Michael addition and subsequent tautomerization and
  • intramolecular aminolysis. Under similar conditions, the reaction of 2-imino-2H-chromene-3-carboxamide (228) and tris(2-chloroethyl) phosphite (232) generated 4-amino-1-(2-chloroethoxy)-9b-hydrochromeno[4,3-c][1,2]azaphosphol-3(2H)-one 1-oxide (233) in 30% yield through the Michael addition and subsequent
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Published 22 Jul 2022

An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydropyridine-3-carboxylates

  • Timur O. Zanakhov,
  • Ekaterina E. Galenko,
  • Mikhail S. Novikov and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2022, 18, 738–745, doi:10.3762/bjoc.18.74

Graphical Abstract
  • , contain the fragment of 4-oxo-1,4-dihydropyridine-3-carboxamide [5][6][7]. Finding new synthetic methods for the preparation of derivatives of 4-oxo-1,4-dihydropyridine-3-carboxylic acid are therefore relevant. Some alkyl 6-aryl-2-methyl-4-oxo-1,4-dihydropyridine-3-carboxylates were prepared by refluxing
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Published 23 Jun 2022

Synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylates from deep eutectic mixtures

  • Sangram Gore,
  • Sundarababu Baskaran and
  • Burkhard König

Beilstein J. Org. Chem. 2022, 18, 331–336, doi:10.3762/bjoc.18.37

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  • raltegravir, the first HIV-integrase inhibitor approved by the FDA for the treatment of HIV infection, derived from 5,6-dihydroxypyrimidine-4-carboxamide and N-methyl-4-hydroxypyrimidinone-carboxamide [18] and hydroxypyrimidinone carboxamide derivative P01, a potent inhibitor of Mycobacterium tuberculosis
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Published 22 Mar 2022

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

  • Marco Keller,
  • Karl Sauvageot-Witzku,
  • Franz Geisslinger,
  • Nicole Urban,
  • Michael Schaefer,
  • Karin Bartel and
  • Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

Graphical Abstract
  • highly electrophilic N-acyliminium intermediates [17]. As a special aspect, we used a carbamate unit (instead of the commonly used carboxamide), ending up with 1-benzyl-1,2,3,4-tetrahydroisoquinolines bearing an N-ethoxycarbonyl residue, which in turn was easily converted directly into an N-methyl group
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Published 05 Nov 2021

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

  • Emmanuel T. Oluwabusola,
  • Olusoji O. Adebisi,
  • Fernando Reyes,
  • Kojo S. Acquah,
  • Mercedes De La Cruz,
  • Larry L. Mweetwa,
  • Joy E. Rajakulendran,
  • Digby F. Warner,
  • Deng Hai,
  • Rainer Ebel and
  • Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

Graphical Abstract
  • presence of an oxazoline ring similar to that found in vulnibactin [27]. The key HMBC cross-peaks (Figure 2 and Supporting Information File 1) from H-9 (δH 4.46, J = 7.3 Hz, d) and H-11(δH 4.90, qd, J = 6.3, 7.3 Hz) to carboxamide C-10 (δC 175.6) and C-7 (δC 167.8), confirmed the proposed structure which
  • carboxamide C-10 (δC 172.9) and the quaternary carbon C-16 (δC 140.2), between H2-15 and H-18/20 to the quaternary carbon C-16, and a strong correlation from H-15 and H-19 to C-17/20 (δC 129.9). The new oxazoline derivative 5 was named pseudomonbactin B. The absolute configuration of the threonine residue in
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Published 13 Sep 2021

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

  • Ryan M. Alam and
  • John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

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  • observed > 99% N-1 regioselectivity for 3-carboxymethyl, 3-tert-butyl, 3-COMe, and 3-carboxamide indazoles. Further extension of this optimized (NaH in THF) protocol to various C-3, -4, -5, -6, and -7 substituted indazoles has highlighted the impact of steric and electronic effects on N-1/N-2 regioisomeric
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Published 02 Aug 2021

Development of N-F fluorinating agents and their fluorinations: Historical perspective

  • Teruo Umemoto,
  • Yuhao Yang and
  • Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

Graphical Abstract
  • ] In 1996, the Banks group reported perfluoro[N-fluoro-N-(4-pyridyl)acetamide] (21-3) as a carboxamide analogue of perfluoro[N-fluoro-N-(4-pyridyl)methanesulfonamide] (11-2, see section 1-11) [82]. Its precursor, 21-2, was prepared from pentafluoropyridine by either one of two methods (Scheme 46
  • ). Precursor 21-2 was treated with neat F2 at 10–20 mmHg pressure in acetonitrile at −35 °C to produce the N-F carboxamide 21-3 in 75% yield but the resulting product was a 79:18 mixture of the desired N-F product 21-3 and the protonated compound 21-1. As a reagent N-F carboxamide 21-2 fluorinated electron
  • -rich substrates such as sodium diethyl (phenyl)malonate, 1-morpholinocyclohexene, phenol, and anisole (Scheme 47). The fluorination power of the carboxamide 21-2 was less than that of its N-F sulfonamide analog 11-2. 1-22. N,N’-Difluoro-1,4-diazoniabicyclo[2.2.2]octane salts In 1996, Umemoto and co
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Published 27 Jul 2021
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