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Search for "Groebke–Blackburn–Bienaymé (GBB)" in Full Text gives 10 result(s) in Beilstein Journal of Organic Chemistry.

A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones

  • Ashutosh Nath,
  • John Mark Awad and
  • Wei Zhang

Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92

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  • Ashutosh Nath John Mark Awad Wei Zhang Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA 10.3762/bjoc.21.92 Abstract A new synthetic route initiated with GroebkeBlackburnBienaymé (GBB) followed by N-acylation, intramolecular Diels–Alder
  • modifications of MCRs could generate novel and complex molecular scaffolds [1][2][3][4][5][6][7][8]. Some MCR adducts generated from Ugi, Passerini, Gewald, Biginelli, and GroebkeBlackburnBienaymé (GBB) reactions have been modified to form chemically diverse heterocyclic scaffolds with potential biological
  • (IMDA), and dehydrative re-aromatization reactions for the synthesis of imidazopyridine-fused isoquinolinones is developed. Gaussian computation analysis on the effect of the substitution groups for the IMDA reaction is performed to understand the reaction mechanism. Keywords: GroebkeBlackburn
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Published 13 Jun 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

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  • multicomponent reactions where formaldehyde per se cannot react. For example, in the GroebkeBlackburnBienaymé (GBB) multicomponent reaction, a three-component reaction of heterocyclic amidines 39, aldehydes 40 and isocyanides 41 under acidic catalysis generates heterobicyclic products 42 through a [4 + 1
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Published 13 Mar 2025

Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

  • Kevin Schofield,
  • Shayna Maddern,
  • Yueteng Zhang,
  • Grace E. Mastin,
  • Rachel Knight,
  • Wei Wang,
  • James Galligan and
  • Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

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  • (Scheme 8) [47]. The GroebkeBlackburnBienaymé (GBB) reaction is an intramolecular variant of the Ugi reaction where the intermediate nitrilium ion is intercepted by heteroatoms from the amino-heterocyclic input. Discovered in 1998, and reported independently by three different research groups, it is a
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Published 06 Sep 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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  • /bjoc.20.162 Abstract The GroebkeBlackburnBienaymé (GBB) three-component reaction, discovered in 1998, is a very efficient strategy to assemble imidazo[1,2-a]-heterocycles starting from amidines, aldehydes and isocyanides. This review aims to exhaustively describe innovative aspects of this reaction
  • ; Introduction The Groebke-Blackburn-Bienaymé (GBB) three-component reaction has been discovered in 1998 and during the course of the first two decades has emerged as one of the most exploited isocyanide-based MCRs, with more than 200 original publications reported and exhaustively reviewed by Boltjes and
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Published 01 Aug 2024

Generation of multimillion chemical space based on the parallel Groebke–Blackburn–Bienaymé reaction

  • Evgen V. Govor,
  • Vasyl Naumchyk,
  • Ihor Nestorak,
  • Dmytro S. Radchenko,
  • Dmytro Dudenko,
  • Yurii S. Moroz,
  • Olexiy D. Kachkovsky and
  • Oleksandr O. Grygorenko

Beilstein J. Org. Chem. 2024, 20, 1604–1613, doi:10.3762/bjoc.20.143

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  • purposes [1][2][3][4][5][6]. Isonitrile-based multicomponent reactions, such as the GroebkeBlackburnBienaymé (GBB) reaction, is an important tool in chemical synthesis providing easy access to a huge compound diversity and complexity [7][8][9][10][11][12][13][14][15][16][17]. Essentially, the GBB
  • (sEH) inhibitors [50], HIV-1 non-nucleoside reverse transcriptase inhibitors [51], or potential agents against visceral leishmaniasis [52] were found (Figure 8). Conclusion The GroebkeBlackburnBienaymé (GBB) reaction, a three-component condensation of amino heterocycles, aldehydes, and isonitriles
  • database. GroebkeBlackburnBienaymé (GBB) reaction. A) Parallel GBB reaction and B) examples of library members 4 obtained (relative configurations are shown). Supporting Information The Supporting Information for this article contains structures of reactants 1–3, experimental details on the parallel
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Published 16 Jul 2024

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

  • Oleksandr V. Kolomiiets,
  • Alexander V. Tsygankov,
  • Maryna N. Kornet,
  • Aleksander A. Brazhko,
  • Vladimir I. Musatov and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

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  • been described till today: Ugi and Ugi, azido-Ugi and Ugi, Ugi and Passerini, GroebkeBlackburnBienaymé (GBB-3CR) and Ugi, GBB-3CR and GBB-3CR, GBB-3CR and Passerini, Orru and Ugi, Orru and Passerini [1] (Scheme 1). However, the issue of whether certain isocyanide multicomponent reactions can be
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Published 26 May 2023

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

  • Nisha Devi and
  • Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

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  • -3 position. Our group has previously explored 1-formyl-β-carbolines and 3-formyl-β-carbolines for the generation of β-carboline-imidazo[1,2-a]azine conjugates at C-1 as well as C-3 position by the application of the GroebkeBlackburnBienaymé (GBB) multicomponent approach [46][47]. Our research
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Published 26 Jul 2022

Selectivity in multiple multicomponent reactions: types and synthetic applications

  • Ouldouz Ghashghaei,
  • Francesca Seghetti and
  • Rodolfo Lavilla

Beilstein J. Org. Chem. 2019, 15, 521–534, doi:10.3762/bjoc.15.46

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  • prone to suffer the same transformation. Relevant examples are shown in Scheme 7. Terephthalaldehyde is capable of undergoing sequential MCRs in a selective manner with two different sets of reactants. In this way, a variety of transformations involving GroebkeBlackburnBienaymé (GBB)/Hantzsch, and
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Published 21 Feb 2019

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

  • Taofeng Shao,
  • Zhiming Gong,
  • Tianyi Su,
  • Wei Hao and
  • Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

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  • combination of the Ugi reaction with other transformations proved to be powerful strategies for the efficient synthesis of novel heterocycles. In 1998, the GroebkeBlackburnBienaymé (GBB) reaction, an Ugi-3CR variant was discovered by three groups independently [36][37][38]. The GBB reaction of an amidine
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Published 04 May 2017

One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

  • Bo Yang,
  • Chuanye Tao,
  • Taofeng Shao,
  • Jianxian Gong and
  • Chao Che

Beilstein J. Org. Chem. 2016, 12, 1487–1492, doi:10.3762/bjoc.12.145

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  • scaffolds can be constructed in great diversity by a multicomponent reaction of amidines, aldehydes and isocyanides. This MCR, a variant of the Ugi reaction [24][25], was discovered independently by three groups and is known as the GroebkeBlackburnBienaymé (GBB) reaction [26][27][28][29]. The reaction
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Published 18 Jul 2016
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