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Search for "7-azabenzotriazole" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.

Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

  • Romain Pierre,
  • Anne Brethon,
  • Sylvain A. Jacques,
  • Aurélie Blond,
  • Sandrine Chambon,
  • Sandrine Talano,
  • Catherine Raffin,
  • Branislav Musicki,
  • Claire Bouix-Peter,
  • Loic Tomas,
  • Gilles Ouvry,
  • Rémy Morgentin,
  • Laurent F. Hennequin and
  • Craig S. Harris

Beilstein J. Org. Chem. 2021, 17, 156–165, doi:10.3762/bjoc.17.16

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  • investment in route scouting and optimization. This full paper focuses on the synthesis issues that we encountered during our route exploration and the original solutions we found that helped us to identify two optimized library-style processes to prepare our large kinase inhibitor library. Keywords: 7
  • -azabenzotriazole; hinge-binder; ionic hydrogenation; library; pyridine-2(1H)-one; Introduction During a recent medicinal chemistry program targeting a kinase to treat skin disorders, we identified the 4-amino-3-carboxamide disubstituted pyridine-2(1H)-one motif (1) as an interesting starting point. Recently, both
  • 12% of desired pyridine-2-(1H)-one 22 was observed (Scheme 4). Despite literature analogies being scarce in this area [13][14], we propose that the reaction could occur through 2 possible pathways. The first proposition concerns the direct reduction of the N(3)=N(2) double bond of the 7
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Published 18 Jan 2021

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

  • Małgorzata Urbańczyk,
  • Michał Jewgiński,
  • Joanna Krzciuk-Gula,
  • Jerzy Góra,
  • Rafał Latajka and
  • Norbert Sewald

Beilstein J. Org. Chem. 2019, 15, 1581–1591, doi:10.3762/bjoc.15.162

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  • -diazabicyclo[5.4.0]undec-7-ene (DBU) in NMP, which were shaken with the resin for 2 hours, and the reaction was repeated. Modified PS-Sieber resin was loaded manually with Fmoc-ʟ-Ala-OH or Fmoc-ᴅ-Ala-OH (4 equiv), 1-hydroxy-7-azabenzotriazole (HOAt, 4 equiv), O-(7-azabenzotriazol-1-yl)-N,N,N’,N
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Published 16 Jul 2019

Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion

  • Susanne Huhmann,
  • Anne-Katrin Stegemann,
  • Kristin Folmert,
  • Damian Klemczak,
  • Johann Moschner,
  • Michelle Kube and
  • Beate Koksch

Beilstein J. Org. Chem. 2017, 13, 2869–2882, doi:10.3762/bjoc.13.279

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  • for 1 h each. The fluorinated amino acids and coupling reagents 1-hydroxy-7-azabenzotriazole (HOAt)/DIC were used in 1.2-fold excess, and the coupling was carried out manually one time overnight. In the case of an insufficient coupling, the coupling was repeated for 3 h with 0.5 equivalents. Prior to
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Published 22 Dec 2017

(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues

  • Armin de Meijere,
  • Sergei I. Kozhushkov,
  • Dmitrii S. Yufit,
  • Christian Grosse,
  • Marcel Kaiser and
  • Vitaly A. Raev

Beilstein J. Org. Chem. 2014, 10, 2844–2857, doi:10.3762/bjoc.10.302

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  • = 4-dimethylaminopyridine, EDC = N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, HATU = O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, HOAt = 7-aza-1-hydroxybenzotriazole, MeZ = (4-methylbenzyl)oxycarbonyl, Z = benzyloxycarbonyl. Synthesis of hormaomycin
  • °C, 1 h; v) HATU, DIEA, 2,4,6-collidine, CH2Cl2, 20 °C, 4 h; vi) MgBr2·Et2O, EtSH, CH2Cl2, 20 °C, 3.5 h. DIEA = N,N-diisopropylethylamine, HATU = O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, HOAt = 7-aza-1-hydroxybenzotriazole, MeZ = (4-methylbenzyl)oxycarbonyl, MOM
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Published 03 Dec 2014

Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications

  • Mahesh K. Lakshman,
  • Manish K. Singh,
  • Mukesh Kumar,
  • Raghu Ram Chamala,
  • Vijayender R. Yedulla,
  • Domenick Wagner,
  • Evan Leung,
  • Lijia Yang,
  • Asha Matin and
  • Sadia Ahmad

Beilstein J. Org. Chem. 2014, 10, 1919–1932, doi:10.3762/bjoc.10.200

Graphical Abstract
  • purified material to those reported [35] for 1-methoxy-1H-4-azabenzotriazole (1-methoxy-1H-[1,2,3]triazolo[4,5-b]pyridine) and 1-methoxy-1H-7-azabenzotriazole (3-methoxy-3H-[1,2,3]triazolo[4,5-b]pyridine) did not allow for ready identification. A NOE experiment did not result in observable interactions of
  • the OMe resonance with the aromatic system. Because neither experiment allowed for unambiguous discrimination between the two structures, 1-methoxy-1H-7-azabenzotriazole was prepared via a known procedure [35]. The chemical shifts for the aromatic protons in the authentic 1-methoxy-1H-7
  • -azabenzotriazole prepared, the product obtained from the reaction of At-OTs and MeOH, as well as the literature data are shown in Table 3. From the Δδ values in this table, it becomes clear that the product obtained in Scheme 4 is in fact 1-methoxy-1H-7-azabenzotriazole. Additionally, the melting point of this
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Published 19 Aug 2014

Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

  • Mathieu L. Lepage,
  • Alessandra Meli,
  • Anne Bodlenner,
  • Céline Tarnus,
  • Francesco De Riccardis,
  • Irene Izzo and
  • Philippe Compain

Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

Graphical Abstract
  • (11 equiv). * Residual solvent peak for CDCl3. • and X are assigned to protons a or b. Monovalent models 11 and 7-valent DNJ derivatives 12. Sub-monomer approach for the synthesis of cyclopeptoids 2–4: DIPEA = N,N-diisopropylethylamine; DIC = N,N’-diisopropylcarbodiimide; HATU O-(7-azabenzotriazole-1
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Published 23 Jun 2014

Automated solid-phase peptide synthesis to obtain therapeutic peptides

  • Veronika Mäde,
  • Sylvia Els-Heindl and
  • Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

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  • carbodiimides (DCC, DIC), classical auxiliary nucleophiles (HOBt, HOAt (1-hydroxy-7-azabenzotriazole) [56]) to uronium reagents (HATU (N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide) [56], TBTU (N-[(1H-benzotriazol-1-yl)(dimethylamino
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Review
Published 22 May 2014

Stereoselective synthesis of four possible isomers of streptopyrrolidine

  • Debendra K. Mohapatra,
  • Barla Thirupathi,
  • Pragna P. Das and
  • Jhillu S. Yadav

Beilstein J. Org. Chem. 2011, 7, 34–39, doi:10.3762/bjoc.7.6

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  • lactamization of 8a, almost similar yields were obtained for 8b), afforded (4R,5R)-streptopyrrolidine (1) and (4S,5R)-streptopyrrolidine (2) in good to excellent overall yield (Scheme 3). From all of the conditions investigated, Zr(OtBu)4 in presence of 1-hydroxy-7-azabenzotriazole (HOAt) gave the best result
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Published 10 Jan 2011

Synthesis of glycosylated β3-homo-threonine conjugates for mucin-like glycopeptide antigen analogues

  • Florian Karch and
  • Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2010, 6, No. 47, doi:10.3762/bjoc.6.47

Graphical Abstract
  • ′,N′-tetramethyluronium hexafluorophosphate, HOBt = N-hydroxybenzotriazole, DIPEA = diisopropylethylamine, HATU = O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, HOAt = N-hydroxy-7-azabenzotriazole, NMM = N-methylmorpholine, TIS = triisopropylsilane. Supporting
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Published 12 May 2010
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