Literature DB >> 20131775

Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: a simple and direct synthesis of functionalized pyrroles.

Sukhendu Maiti1, Srijit Biswas, Umasish Jana.   

Abstract

A simple, convenient, and multicomponent coupling strategy for the synthesis of highly functionalized pyrroles catalyzed by iron(III) salts has been developed. This strategy demonstrated four-component coupling reactions of 1,3-dicarbonyl compounds, amines, aromatic aldehydes, and nitroalkanes without an inert atmosphere. This methodology provides an alternative approach for easy access of highly substituted pyrroles in moderate to very good yields using four simple and readily available building blocks via one-pot tandem reaction. Notably, this method is very cheap, straightforward, and environmentally friendly compared to the existing methods.

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Year:  2010        PMID: 20131775     DOI: 10.1021/jo902661y

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  12 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  A sustainable catalytic pyrrole synthesis.

Authors:  Stefan Michlik; Rhett Kempe
Journal:  Nat Chem       Date:  2013-01-20       Impact factor: 24.427

3.  One-pot multicomponent synthesis of diversely substituted 2-aminopyrroles. A short general synthesis of rigidins A, B, C, and D.

Authors:  Liliya V Frolova; Nikolai M Evdokimov; Kathryn Hayden; Indranil Malik; Snezna Rogelj; Alexander Kornienko; Igor V Magedov
Journal:  Org Lett       Date:  2011-01-26       Impact factor: 6.005

4.  VCl3 catalyzed imine-based multicomponent reactions for the facile access of functionalized tetrahydropyridines and β-amino carbonyls.

Authors:  Suman Pal; Lokman Hakim Choudhury; Tasneem Parvin
Journal:  Mol Divers       Date:  2011-11-01       Impact factor: 2.943

5.  DBU-mediated annulation of 2-aryl-3-nitro-2H-chromenes with 1,3-cyclohexanediones for the synthesis of benzofuro[2,3-c]chromenone derivatives.

Authors:  Chenlu Dai; Zengyang Xie; Xushun Qing; Naili Luo; Cunde Wang
Journal:  Mol Divers       Date:  2019-03-23       Impact factor: 2.943

6.  Revisit to the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives in lactic acid media as a green solvent and catalyst.

Authors:  Dilek Akbaslar; E Sultan Giray; Oztekin Algul
Journal:  Mol Divers       Date:  2020-09-27       Impact factor: 2.943

7.  RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones via Annulation of N-Methoxyamides and Nitroalkenes.

Authors:  Tyler J Potter; Yuantao Li; Michael D Ward; Jonathan A Ellman
Journal:  European J Org Chem       Date:  2018-06-11

8.  Direct functionalization of (un)protected tetrahydroisoquinoline and isochroman under iron and copper catalysis: two metals, two mechanisms.

Authors:  Michael Ghobrial; Michael Schnürch; Marko D Mihovilovic
Journal:  J Org Chem       Date:  2011-10-05       Impact factor: 4.354

9.  Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

Authors:  Manjeet K Majhail; Paul M Ylioja; Michael C Willis
Journal:  Chemistry       Date:  2016-04-23       Impact factor: 5.236

10.  Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions.

Authors:  Sudipta Pathak; Kamalesh Debnath; Animesh Pramanik
Journal:  Beilstein J Org Chem       Date:  2013-11-04       Impact factor: 2.883

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