Literature DB >> 34652591

Synthesis of functionalized pyrrole derivatives via diverse cyclization of azomethine ylide and olefins.

Saman Sayebani1, Hossein Eshghi2, Maryam Naeimabadi1.   

Abstract

The azomethine ylides are generally used in 1,3-dipolar cycloadditions with various dipolarophiles. In this work, a new and diverse route has been developed for the azomethine ylides, for synthesis of novel pyrrole derivatives. The azomethine ylide, produced via C-H activation of unreactive C(sp3)-H bond of 2-methylquinoline, by molecular iodine, in the presence of pyridine. Herein, we represent novel pyrrole derivatives, synthesized from the reaction of pyridinium ylide with olefins, which formed via a reaction of isatin, dialkyl acetylenedicarboxylate derivatives and pyridine as a base in moderate to excellent yields. Various features of this cyclization, discussed.
© 2021. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

Entities:  

Keywords:  Azomethine ylide; Diverse cyclization reaction; Pyridine; Pyrrole-based scaffolds; Tandem reaction

Mesh:

Substances:

Year:  2021        PMID: 34652591     DOI: 10.1007/s11030-021-10328-x

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   3.364


  6 in total

1.  Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors:  Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  Synthesis of new class of alkyl azarene pyridinium zwitterions via iodine mediated sp3 C-H bond activation.

Authors:  Atul Kumar; Garima Gupta; Suman Srivastava
Journal:  Org Lett       Date:  2011-11-22       Impact factor: 6.005

3.  Targeting isoprenoid biosynthesis for drug discovery: bench to bedside.

Authors:  Eric Oldfield
Journal:  Acc Chem Res       Date:  2010-09-21       Impact factor: 22.384

4.  Access to Fluorazones by Intramolecular Dehydrative Cyclization of Aromatic Tertiary Amides: A Synthetic and Mechanistic Study.

Authors:  Béla Mátravölgyi; Tamás Hergert; Erika Bálint; Péter Bagi; Ferenc Faigl
Journal:  J Org Chem       Date:  2018-02-05       Impact factor: 4.354

Review 5.  Understanding and exploiting C-H bond activation.

Authors:  Jay A Labinger; John E Bercaw
Journal:  Nature       Date:  2002-05-30       Impact factor: 49.962

6.  Design, synthesis, and evaluation of novel thienopyrrolizinones as antitubulin agents.

Authors:  Vincent Lisowski; Stéphane Léonce; Laurence Kraus-Berthier; Jana Sopková-de Oliveira Santos; Alain Pierré; Ghanem Atassi; Daniel-Henri Caignard; Pierre Renard; Sylvain Rault
Journal:  J Med Chem       Date:  2004-03-11       Impact factor: 7.446

  6 in total
  1 in total

Review 1.  1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments.

Authors:  Fatemeh Rostami Miankooshki; Mohammad Bayat; Shima Nasri; Narges Habibi Samet
Journal:  Mol Divers       Date:  2022-08-04       Impact factor: 3.364

  1 in total

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