Literature DB >> 25652577

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds.

Upendra K Sharma1, Nandini Sharma, Dipak D Vachhani, Erik V Van der Eycken.   

Abstract

The Ugi-4CR is by far one of the most successful multicomponent reactions leading to high structural diversity and molecular complexity. However, the reaction mostly affords a linear peptide backbone, enabling post-Ugi transformations as the only solution to rigidify the Ugi-adduct into more drug like species. Not surprisingly, the development of these transformations, leading to new structural frameworks, has expanded rapidly over the last few years. As expected, palladium-catalyzed reactions have received the foremost attention, yet other metals, particularly gold complexes, are fast catching up. This tutorial review outlines the developments achieved in the past decade, highlighting the modifications that are performed in a sequential or domino fashion with emphasis on major concepts, synthetic applications of the derived products as well as mechanistic aspects.

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Year:  2015        PMID: 25652577     DOI: 10.1039/c4cs00253a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  15 in total

1.  An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.

Authors:  Zhengbo Zhu; Daniel Seidel
Journal:  Org Lett       Date:  2016-01-19       Impact factor: 6.005

2.  Synthesis of fused polycyclic β-carboline derivatives using Ugi-4CR followed by cascade cyclization.

Authors:  Vipin Kumar; Anjali Saxena; Ranjan Patra; Devalina Ray; Hong-Yu Li; Biswajit Saha
Journal:  Mol Divers       Date:  2022-06-02       Impact factor: 2.943

Review 3.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

4.  Fluorinated polymer surfactants bearing an alternating peptide skeleton prepared by three-component polycondensation.

Authors:  Y Koyama; A B Ihsan; T Taira; T Imura
Journal:  RSC Adv       Date:  2018-02-16       Impact factor: 4.036

5.  Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction.

Authors:  Samantha Caputo; Andrea Basso; Lisa Moni; Renata Riva; Valeria Rocca; Luca Banfi
Journal:  Beilstein J Org Chem       Date:  2016-01-26       Impact factor: 2.883

6.  Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids.

Authors:  Răzvan C Cioc; Verónica Estévez; Daan J van der Niet; Christophe M L Vande Velde; Nikolaus G Turrini; Mélanie Hall; Kurt Faber; Eelco Ruijter; Romano V A Orru
Journal:  European J Org Chem       Date:  2017-03-08

7.  Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles.

Authors:  Thimmalapura M Vishwanatha; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling
Journal:  J Org Chem       Date:  2017-08-25       Impact factor: 4.354

8.  Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions).

Authors:  Art Kruithof; Christophe M L Vande Velde; Eelco Ruijter; Romano V A Orru
Journal:  Molecules       Date:  2017-03-28       Impact factor: 4.411

9.  Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

Authors:  Amarendar Reddy Maddirala; Peter R Andreana
Journal:  Beilstein J Org Chem       Date:  2018-04-18       Impact factor: 2.883

10.  Hexafluoroisopropanol as the Acid Component in the Passerini Reaction: One-Pot Access to β-Amino Alcohols.

Authors:  Jordy M Saya; Rayan Berabez; Pim Broersen; Imme Schuringa; Art Kruithof; Romano V A Orru; Eelco Ruijter
Journal:  Org Lett       Date:  2018-06-15       Impact factor: 6.005

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