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Search for "tetrazole" in Full Text gives 66 result(s) in Beilstein Journal of Organic Chemistry.

Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium

  • Dāgs Dāvis Līpiņš,
  • Andris Jeminejs,
  • Una Ušacka,
  • Anatoly Mishnev,
  • Māris Turks and
  • Irina Novosjolova

Beilstein J. Org. Chem. 2024, 20, 675–683, doi:10.3762/bjoc.20.61

Graphical Abstract
  • tetrazole tautomeric equilibrium directs the nucleofugal sulfinate from the first step to replace chloride at the C2 position. This transformation is effective with quinazolines bearing electron-rich substituents. Therefore, the title transformations are demonstrated on the 6,7-dimethoxyquinazoline core
  • : aromatic nucleophilic substitution; azide–tetrazole equilibrium; 4-azido-2-sulfonylquinazolines; quinazolines; sulfonyl group dance; Introduction The quinazoline core is a privileged structure with a wide range of applications. Quinazoline derivatives exhibit a broad spectrum of biological activities
  • azide–tetrazole equilibrium of product 12a was initiated, revealing a singular form present in all solvents. Despite attempts to increase the amount of the azide form with the increase of the temperature in NMR experiments [27], no observable alteration in the tautomeric equilibrium was observed. FTIR
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Published 28 Mar 2024

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

  • Milandip Karak,
  • Cian R. Cloonan,
  • Brad R. Baker,
  • Rachel V. K. Cochrane and
  • Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

Graphical Abstract
  • ]. The ratio of α/β-anomers in compound 5 was found to be influenced by the reaction conditions, consistently favoring the β-anomer. Further transformation of compound 5 involved α-selective phosphite formation using dibenzyl N,N-diisopropylphosphoramidite and 5-(ethylthio)-1H-tetrazole. The resulting α
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Published 06 Feb 2024

N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction

  • Grigory Kantin,
  • Pavel Golubev,
  • Alexander Sapegin,
  • Alexander Bunev and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136

Graphical Abstract
  • pyrazole derivatives (including indazole), benzimidazole, 1,2,3-triazole, indole, carbazole, indoline, quinazoline, and isoquinoline. Nevertheless, many heterocyclic motifs still remain beyond the attention of researchers. For example, glutarimides that incorporate tetrazole and 1,2,4-triazole substituents
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Published 07 Dec 2023

Selectivity control towards CO versus H2 for photo-driven CO2 reduction with a novel Co(II) catalyst

  • Lisa-Lou Gracia,
  • Philip Henkel,
  • Olaf Fuhr and
  • Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

Graphical Abstract
  • (NCS)2(NN) complexes, where NN is a chelating diimine compound such as pyridyl-tetrazole [44], or a pyridine-oxazole [45]. The bond lengths are very similar when comparing the polymorphs 1a and 1b. Nevertheless, the bond angles vary significantly (see Table S2 in Supporting Information File 1
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Published 17 Nov 2023

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

Graphical Abstract
  • 1H-tetrazole to produce the trialkyl phosphite 8.3 that was oxidized with tert-butyl hydroperoxide to produce phosphate 8.4. Then, β-elimination of the cyanoethyl protecting group produced PAF with a global yield of 70%. The limit of this method arises from the instability of the precursor 8.1 for
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Published 08 Sep 2023

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

  • Ksenia Malkova,
  • Andrey Bubyrev,
  • Stanislav Kalinin and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 800–807, doi:10.3762/bjoc.19.60

Graphical Abstract
  • carbonyl group deactivation. Furthermore, while implementing the protocol for 2-azidoquinoline-3-carbaldehyde (1t), a low conversion of this reagent was detected, which can be explained by the fact that 1t tends to exist in the inactive tetrazole form. In addition, our attempt to involve Boc-protected
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Published 09 Jun 2023

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

  • Laura Holzhauer,
  • Chloé Liagre,
  • Olaf Fuhr,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

Graphical Abstract
  • ; tetrazole; triazole; Introduction Quinoxalines are amongst the most versatile N-heterocyclic compounds, combining a straightforward synthesis with a diverse set of possible functionalizations and a wide range of applications in drug development and materials sciences [1]. Different quinoxaline derivatives
  • ). Condensation to the corresponding quinoxalinone and subsequent chlorination was followed by introduction of the tetrazole moiety into the molecule via sodium azide to yield 11a–e. Alternatively, 4-chlorotetrazolo[1,5-a]quinoxaline (11f) was obtained after reaction of 2,3-dichloroquinoxaline (10f) with
  • ). Increasing the amount of alkyne 4 increases the probability of the alkyne being coordinated in contrast to the tetrazole, which leads to launching of the CuAAC cycle. The probability of coordination on the tetrazole should also be indirectly impacted by this. However, the imidazole formation is only slightly
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Published 24 Aug 2022

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Graphical Abstract
  • oxathiolane propionate derivative 43 by using Mucor miehei lipase, which affords (−)-enantiomer 44 as residual substrate. This enantioenriched precursor was useful to obtain the pure corresponding nucleoside analogue. Faury and co-workers [50] synthesized the tetrazole analogues of 1,3-oxathiolane nucleosides
  • '-thiacytidine derivatives. The tetrazole analogues of 1,3-oxathiolane nucleosides were synthesized by Faury et al. [50]. N-Glycosylation of silylated tetrazole with 1,3-oxathiolane precursor 45 in the presence of titanium tetrachloride or TMSOTf, followed by deprotection in methanolic ammonia gave the final
  • nucleoside 97 (Scheme 42). Unfortunately, the introduction of a tetrazole ring to the oxathiolane moiety did not result in any anti-HIV activity and higher cytotoxicity. The synthesis of N4-substituted analogue 99 of 2',3'-dideoxy-3'-thiacytosine was discovered by Camplo et al. (Scheme 43) [77]. The prodrug
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Published 04 Nov 2021

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction

  • Dušan Đ. Škorić,
  • Olivera R. Klisurić,
  • Dimitar S. Jakimov,
  • Marija N. Sakač and
  • János J. Csanádi

Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174

Graphical Abstract
  • different ketone and enone precursors from cholic acid, deoxycholic acid, and chenodeoxycholic acid was established. Newly obtained tetrazole derivatives were characterized by NMR and X-ray diffraction spectroscopy. In a number of cases, preliminary antiproliferative tests of new compounds showed strong and
  • bile acids, derivatives with altered hydrophobicity are being studied [12][13][14]. The tetrazole moiety can be found in many biologically active compounds, and monosubstituted tetrazole is being used in medicinal chemistry as a bioisostere of carboxylic acid [15] because it increases the lipophilicity
  • ]. The main approach in the synthesis of the tetrazoles is 1,3-dipolar cycloaddition between azide and nitrile. These reactions often follow the principles of “click” chemistry [20]. Although the formation of tetrazole in the Schmidt reaction of ketones was noted in the original study by Schmidt himself
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Published 20 Oct 2021

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

  • Eleni Dimitriou and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

Graphical Abstract
  • mannuronic acid building blocks, appropriately modified at the carboxylate C6 position with a bioisosteric tetrazole. Thioglycosides containing a protected C6-tetrazole are accessed from a C6-nitrile, through dipolar cycloaddition using NaN3 with n-Bu2SnO. We also demonstrate access to orthogonally C4
  • -protected donors, suitable for iterative oligosaccharide synthesis. The development of these building blocks is showcased to access anomeric 3-aminopropyl- and 1-phosphate free sugars containing this non-native motif. Keywords: alginate; glycosyl 1-phosphate; non-native monosaccharide; tetrazole; uronate
  • , tetrazole (Figure 1b). As an established bioisostere for a carboxylic acid, tetrazole has found significant application within medicinal chemistry [12]. The aromatic tetrazole ring is considered a non-classical bioisostere, differing in size and number of atoms to the carboxylic acid. The functional group
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Published 05 Jul 2021

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

  • Greta Utecht-Jarzyńska,
  • Karolina Nagła,
  • Grzegorz Mlostoń,
  • Heinz Heimgartner,
  • Marcin Palusiak and
  • Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

Graphical Abstract
  • reported in the 1960s [17]. The latter 1,3-dipole was generated thermally from the respective tetrazole derivative 3, and the observed [3 + 2]-cycloadditions occurred chemoselectively to provide fused pyrazoles of the type 4 as exclusive products (Scheme 1). This type of cycloaddition attracted
  • , generated from tetrazole 3, reported by Huisgen et al. [17]. Selected applications of trifluoroacetonitrile imines 7 in the synthesis of S-containing 5- and 6-membered heterocycles. Synthesis of [3 + 2]-cycloadducts 9a–l derived from CF3-substituted nitrile imines 7a–h and 1,4-quinones 1a and 1b. Thermal
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Published 28 Jun 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Graphical Abstract
  • the catalyst expense. As enantioselective catalysts require expensive structural modifications, the possibility of immobilisation would facilitate catalyst recovery/recycle and drastically reduce the cost of the associated process. In 2012, silica-supported 5-(pyrrolidin-2-yl)tetrazole 63 was used to
  • ), column robustness/ease of recyclability and the facile nature of reaction condition and substrate screening. To increase the greenness and reduce the consumption of the catalyst, Yamamoto and Nakashima have recently developed a proline tetrazole 51 packed-bed reactor system, exploiting the low solubility
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Published 18 May 2021

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

  • Christopher Liczner,
  • Kieran Duke,
  • Gabrielle Juneau,
  • Martin Egli and
  • Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

Graphical Abstract
  • )-modified oligonucleotides was first described in 1991 by the Caruthers group [84]. Typically, each 2'-deoxynucleoside 3'-phosphorothioamidite is prepared by phosphitylating the protected nucleosides with tris(pyrrolidino)phosphine under tetrazole catalysis, followed by immediate treatment with
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Published 28 Apr 2021

Synthesis and properties of oligonucleotides modified with an N-methylguanidine-bridged nucleic acid (GuNA[Me]) bearing adenine, guanine, or 5-methylcytosine nucleobases

  • Naohiro Horie,
  • Takao Yamaguchi,
  • Shinji Kumagai and
  • Satoshi Obika

Beilstein J. Org. Chem. 2021, 17, 622–629, doi:10.3762/bjoc.17.54

Graphical Abstract
  • the middle position of 12-mer oligonucleotides (Table 1). The oligonucleotide synthesis was performed using an automated DNA synthesizer following the established synthetic method for GuNA[Me]-T-modified oligonucleotides [20]. 5-(Ethylthio)-1H-tetrazole (ETT) was used as an activator for the coupling
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Published 04 Mar 2021

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

  • Vladislav A. Budevich,
  • Sergei V. Voitekhovich,
  • Alexander V. Zuraev,
  • Vadim E. Matulis,
  • Vitaly E. Matulis,
  • Alexander S. Lyakhov,
  • Ludmila S. Ivashkevich and
  • Oleg A. Ivashkevich

Beilstein J. Org. Chem. 2021, 17, 385–395, doi:10.3762/bjoc.17.34

Graphical Abstract
  • -(methylsulfonyl)-1-phenyl-1H-tetrazole with substitution of bromine and methylsulfonyl groups giving the corresponding tetrazolium salts or conjugate aminides. The obtained mesoionic tetrazoles have been characterized by elemental analysis, FTIR, NMR, and UV–vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert
  • : aminotetrazoles; DFT; mesoionic compounds; UV–vis spectra; X-ray analysis; Introduction 5-Aminotetrazoles are one of the most available and valuable tetrazole derivatives. So, due to the thermal stability and high nitrogen content the parent 5-aminotetrazole (1, Figure 1) is of practical interest as a gas
  • -generator and blowing agent [1][2]. Moreover, it is a useful building block in organic synthesis, including various multicomponent reactions opening the way to diverse fused heterocycles [3]. Salts with anionic tetrazole, i.e., aminotetrazolates 2, and cationic ones, i.e., aminotetrazolium salts 3, are
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Published 08 Feb 2021

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

  • Michał M. Więcław and
  • Bartłomiej Furman

Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

Graphical Abstract
  • Michal M. Wieclaw Bartlomiej Furman Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland 10.3762/bjoc.17.12 Abstract Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a
  • products. Finally, some surprising observations regarding the mechanism of their formation were made. Keywords: amide functionalization; iminosugars; Schwartz’s reagent; tetrazole; Introduction The transformation of an amide into another chemical moiety in a controlled manner is not a trivial task
  • molecule incorporating both an iminosugar and a tetrazole fragment is of particular interest, due to the interesting properties of both moieties (Figure 1). It is probably hard to overestimate the importance of sugar scaffolds in nature, and we believe that it speaks for itself, however, a significance of
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Published 13 Jan 2021

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

  • Marek Baráth,
  • Jana Jakubčinová,
  • Zuzana Konyariková,
  • Stanislav Kozmon,
  • Katarína Mikušová and
  • Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

Graphical Abstract
  • investigations on their more stable analogs resulted in the synthesis of stable 1-O-phoshono-β-ᴅ-psicofuranosyl sulfone, which was prepared by a simultaneous phosphorylation and oxidation of ethyl 2-thio-β-ᴅ-psicofuranoside with dibenzyl N,N-dimethylphosphoramidite catalyzed by 1H-tetrazole and followed by
  • -fructofuranose derivatives 1 and started from the four known alcohols 4α, 5α, 5β and 6α [17]. Initial treatment of these alcohols with commercially available dibenzyl N,N-dimethylphosphoramidite as phosphorylating agent catalyzed by 1H-tetrazole and followed by direct oxidation with an excess of 3
  • by GlfT2. Reagents and conditions: a) 1. (BnO)2P-NMe2, 1H-tetrazole, 0 °C→rt, 1 h, 2. m-CPBA, 0 °C→rt, 1.5‒2 h; b) H2, 10% Pd/C, MeOH, rt, 3‒4 h. Reagents and conditions: a) PivCl, pyridine, CH2Cl2, rt, overnight; b) BnBr, NaOH, TBAB, THF, reflux, 3 h. Reagents and conditions: a) EtSH, BF3∙OEt2
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Published 27 Jul 2020

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

  • Giovanni Picca,
  • Markus Probst,
  • Simon M. Langenegger,
  • Oleg Khorev,
  • Peter Bütikofer,
  • Anant K. Menon and
  • Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

Graphical Abstract
  • t-BuOOH, and finally, the protecting groups were removed under basic conditions to give either MPC-1 or MPC-2 as ammonium salts. ETT = 5-(ethylthio)-1H-tetrazole. Preparation of mannosyl phosphoramidites. Starting from 2,3,4,6-tetra-O-acetyl-β-ᴅ-mannopyranose (β-4Ac-Man), the phosphitylation using 2
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Published 20 Jul 2020

Microwave-assisted efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

  • Moustafa Sherief Moustafa,
  • Ramadan Ahmed Mekheimer,
  • Saleh Mohammed Al-Mousawi,
  • Mohamed Abd-Elmonem,
  • Hesham El-Zorba,
  • Afaf Mohamed Abdel Hameed,
  • Tahany Mahmoud Mohamed and
  • Kamal Usef Sadek

Beilstein J. Org. Chem. 2020, 16, 1706–1712, doi:10.3762/bjoc.16.142

Graphical Abstract
  • developed by reacting 5-amino-1,2,3,4-tetrazole with aromatic aldehydes and cyanamide in pyridine under controlled microwave heating with high yields. X-ray crystallography confirmed the structure of the obtained products. Keywords: microwave irradiation; N2-(tetrazol-5-yl)-6-aryl/heteroaryl-1,3,5-triazine
  • ]. Tetrazole derivatives are a potent class of heterocyclic compounds with a wide range of biological activities owing to their unique structure. They play an important role not only as a bioisostere of the carboxylic acid group but also as flexible ligands which easily adopt to different binding modes [12][13
  • ]. Tetrazole derivatives exhibit a wide spectrum of biological activities as antibacterial [14], anticancer [15], anti-inflammatory [16], antidiabetic [17], antitubercular [18], and analgesic [19] agents. It is well established that many medical disorders can be caused as a result of defects at more than one
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Published 16 Jul 2020

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

  • Bernd Strehmel,
  • Christian Schmitz,
  • Ceren Kütahya,
  • Yulian Pang,
  • Anke Drewitz and
  • Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

Graphical Abstract
  • with thiol moieties such as phenylmercapto and phenylmercapto-tetrazole substituents resulted in Φf of 7% (compare 64–68) and 3% (compare 78), respectively. Thus, one can roughly draw the following order for the decrease fluorescence quantum yields located at the meso-position: PhO-; Ph- ≥ barbiturate
  • ≥ Ph2N- > PhS- > phenylmercapto tetrazole. Thus, it would be difficult to draw conclusions based on these substituents with respect to their electronic properties. While Ph-O, Ph2N-, and Ph-S- exhibit electron donating properties, barbiturate and phenyl substituents can be seen more or less as electron
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Published 18 Mar 2020

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

  • Sambasivarao Kotha,
  • Gaddamedi Sreevani,
  • Lilya U. Dzhemileva,
  • Milyausha M. Yunusbaeva,
  • Usein M. Dzhemilev and
  • Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

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  • tetrazolium dye, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (МТТ) or yellow tetrazole, to give insoluble formazan, which develops purple color particularly in living cells. Thus, the color gradient can serve to determine the degree of cytostatic activity (shift from proliferation to
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Published 18 Nov 2019

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

Graphical Abstract
  • rhodium(III)-catalyzed intermolecular annulation has been established for the preparation of tetrazole-isoquinolone/pyridone hybrids. Several N-acylaminomethyltetrazoles were reacted with arylacetylenes to form the hybrid products in moderate to very good yields. The method relies on the capacity of the
  • rhodium catalyst to promote C(sp2)–H activation in the presence of a suitable directing group. The Ugi-azide reaction provides broad molecular diversity and enables the introduction of the tetrazole moiety, which may further assist the catalytic reaction by coordinating the metal center. The scope of the
  • . Keywords: C–H activation; cyclization; isoquinolone; multicomponent reaction; tetrazole; Introduction Pyridones and isoquinolones are relevant heterocyclic scaffolds present in numerous bioactive compounds and natural products [1][2][3][4]. Similarly, molecules containing a tetrazole ring exhibit a wide
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Published 16 Oct 2019

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

  • Irina G. Tkachenko,
  • Sergey A. Komykhov,
  • Vladimir I. Musatov,
  • Svitlana V. Shishkina,
  • Viktoriya V. Dyakonenko,
  • Vladimir N. Shvets,
  • Mikhail V. Diachkov,
  • Valentyn A. Chebanov and
  • Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

Graphical Abstract
  • -withdrawing properties of the tetrazole ring, which makes them useful for studying various theoretical issues, e.g., tautomerism [5], intramolecular transformations [6], etc. There are several approaches to the synthesis of 4,7-dihydrotetrazolo[1,5-a]pyrimidines. Two of them make use of 5-aminotetrazole as a
  • accessible by variation of the binucleophilic component 1 (instead of 1, 3-amino-1,2,4-triazole, 2-aminobenzimidazole, 3-aminopyrazoles, 4-amino-1,2,3-triazoles, etc. can be used [13]). However, a relatively low reactivity of amine 1 due to the electron deficiency of the tetrazole ring has been reported
  • several times [5][6]. A third approach (Scheme 1, reaction 3) is completely different and consists of the tetrazole ring formation through cyclization of dihydropyrimidinethiones with sodium azide [14]. Generally, all three approaches allow for the preparation of a broad range of compounds 3 with a wide
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Published 08 Oct 2019

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

  • Iwona E. Głowacka,
  • Aleksandra Trocha,
  • Andrzej E. Wróblewski and
  • Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

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Published 23 Jul 2019

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

  • Shahien Shahsavari,
  • Dhananjani N. A. M. Eriyagama,
  • Bhaskar Halami,
  • Vagarshak Begoyan,
  • Marina Tanasova,
  • Jinsen Chen and
  • Shiyue Fang

Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108

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  • -(ethylthio)-1H-tetrazole as activator instead of the typically used acetic anhydride. Oxidation was performed under standard conditions. The last nucleotide at the 5'-end of ODN was incorporated with a 5'-trityl nucleoside phosphoramidite instead of a 5'-DMTr counterpart. At the end of the synthesis, the 5
  • × 2; coupling, phosphoramidite (0.1 M, MeCN), 5-(ethylthio)-1H-tetrazole (0.25 M, MeCN), 60 s × 3 (or 2); capping, 25 (0.1 M, MeCN) and 5-(ethylthio)-1H-tetrazole (0.25 M, MeCN), 60 s × 3; oxidation, I2 (0.02 M, THF/pyridine/H2O, 70/20/10, v/v/v), 40 s. For incorporating the last nucleoside monomer, a
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Published 20 May 2019
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