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Search for "1H-pyrrole-2,3-diones" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.

Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles

  • Ekaterina A. Lystsova,
  • Maksim V. Dmitriev,
  • Andrey N. Maslivets and
  • Ekaterina E. Khramtsova

Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46

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  • targeted cancer therapy development. Keywords: 1,4-benzothiazine; 1,3-benzothiazole; 1H-pyrrole-2,3-diones; nitrogen heterocycle; sulfur heterocycle; Introduction Pyrrolo[2,1-b][1,3]benzothiazole (PBTA) is an angularly fused sulfur and nitrogen-containing heterocyclic scaffold. Its derivatives are
  •  4). Results and Discussion It is known that [e]-fused 1H-pyrrole-2,3-diones (FPDs) (Figure 2) are versatile synthetic platforms enabling the synthesis of numerous heterocyclic species [33][34][35][36]. They are polyelectrophilic compounds, bearing five electrophilic centers, whose reactivity
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Published 11 May 2023

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles

  • Pavel A. Topanov,
  • Anna A. Maslivets,
  • Maksim V. Dmitriev,
  • Irina V. Mashevskaya,
  • Yurii V. Shklyaev and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2022, 18, 1532–1538, doi:10.3762/bjoc.18.162

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  • , Perm 614990, Russian Federation 10.3762/bjoc.18.162 Abstract There has been developed an easy synthetic approach to spiro[dihydrofuran-2,3'-oxindoles] via a highly diastereoselective formal [4 + 1] cycloaddition reaction of [e]-fused 1H-pyrrole-2,3-diones with diazooxindoles. The described novel
  • heterocyclic systems are heteroanalogues of antimicrobial and antibiofilm fungal metabolites. The developed reaction represents the first example of involving 1H-pyrrole-2,3-diones fused at the [e]-side in a [4 + 1] annulation reaction. Keywords: [4 + 1] annulation; catalyst-free; diazooxindole; 1H-pyrrole
  • ] (Scheme 1). Thus, in the present work, we report a simple, catalyst-free diastereoselective method for the synthesis of dihydrofurans spiro-annulated with an oxindole moiety for the first time. The essence of the method is the use of [e]-fused 1H-pyrrole-2,3-diones (FPDs) as the enone component in a
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Published 10 Nov 2022

Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

  • Aleksandr I. Kobelev,
  • Nikita A. Tretyakov,
  • Ekaterina E. Stepanova,
  • Maksim V. Dmitriev,
  • Michael Rubin and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2019, 15, 2864–2871, doi:10.3762/bjoc.15.280

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  • pyrrole-2-one fragment involving the reaction of [e]-fused 1H-pyrrole-2,3-diones with thioureas was developed. The obtained spiro pseudothiohydantoin derivatives were found to undergo a pseudothiohydantoin–thiohydantoin rearrangement. The reactions were shown to proceed under catalyst-free conditions in
  • spiro-fused to a pharmacologically valuable pyrrole-2-one fragment and to investigate the scope and conditions of their PTR behavior (Scheme 2). Results and Discussion 1H-Pyrrole-2,3-diones fused at [e]-side (FPDs) 1 can be viewed as a versatile polyelectrophilic synthetic platform (Figure 2), enabling
  • developed a divergent approach to pharmaceutically interesting regiomeric thiohydantoins and pseudothiohydantoins spiro-fused to a pyrrole-2-one fragment via the reaction of [e]-fused 1H-pyrrole-2,3-diones with thioureas. The obtained pseudothiohydantoins were found to be prone to undergo a
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Published 27 Nov 2019

Annulation of 1H-pyrrole-2,3-diones by thioacetamide: an approach to 5-azaisatins

  • Aleksandr I. Kobelev,
  • Ekaterina E. Stepanova,
  • Maksim V. Dmitriev and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2019, 15, 364–370, doi:10.3762/bjoc.15.32

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  • of 5-azaisatoic anhydride with cyanides followed by hydrolysis [10], Scheme 1). Herein, we report a distinct synthetic approach to 5-azaisatins via annulation of pyrrole-2,3-dione by a pyridine ring based on an unprecedented interaction of 1H-pyrrole-2,3-diones with thioacetamide (Scheme 1). Results
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Published 07 Feb 2019

Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

  • Alexey Yu. Dubovtsev,
  • Maksim V. Dmitriev,
  • Аndrey N. Maslivets and
  • Michael Rubin

Beilstein J. Org. Chem. 2017, 13, 2179–2185, doi:10.3762/bjoc.13.218

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  • demonstrated, the development of new efficient and highly selective synthetic tools is always desired. From this prospective, we have become greatly interested in the chemistry of 1H-pyrrole-2,3-diones, polyfunctional building blocks that have great potential for the synthesis of heterocyclic structures
  • spirocondensation of 5-alkoxycarbonyl-1H-pyrrole-2,3-diones (serving as 1,2-bis-electrophiles) with cyclic ketazinones (serving as either 1,3-C,N- or 1,3-C,O-bis-nucleophiles). Results and Discussion Previously, we demonstrated a convenient approach towards spiro[indole-3,2’-pyrroles] 3 based on catalyst-free
  • elusive scaffold. Conclusion In conclusion, we discovered a new mode of cyclocondensations with “inverted” regiochemistry of addition, which involved the acid-catalyzed reaction of 5-alkoxycarbonyl-4-aroyl-1H-pyrrole-2,3-diones with cyclohexane-1,3-diones and lead to the formation of bridged 2,5
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Published 19 Oct 2017

Organocatalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors

  • Ming-Liang Zhang,
  • Deng-Feng Yue,
  • Zhen-Hua Wang,
  • Yuan Luo,
  • Xiao-Ying Xu,
  • Xiao-Mei Zhang and
  • Wei-Cheng Yuan

Beilstein J. Org. Chem. 2016, 12, 295–300, doi:10.3762/bjoc.12.31

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  • 100049, China 10.3762/bjoc.12.31 Abstract For the first time, a catalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones was achieved with a chiral bifunctional amine-thiourea as a catalyst possessing multiple hydrogen-bond donors. With this developed method, a range of 3-hydroxy-3-nitromethyl-1H
  • -pyrrol-2(3H)-ones bearing quaternary stereocenters were obtained in acceptable yield (up to 75%) and enantioselectivity (up to 73% ee). Keywords: asymmetric catalysis; bifunctional catalysts; Henry reaction; organocatalysis; 1H-pyrrole-2,3-diones; Introduction Asymmetric organocatalysis has been
  • derivatives exhibit a wide spectrum of biological activities [29]. The reaction of 1H-pyrrole-2,3-diones with various nucleophiles should be a straightforward way to access diverse and interesting 3-substituted-3-hydroxy-1H-pyrrol-2(3H)-ones. A survey of the literature reveals that the study of 1H-pyrrole-2,3
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Published 16 Feb 2016
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