Literature DB >> 19629194

Triflic acid controlled successive annelation of aromatic sulfonamides: An efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles.

Mohammed Abid1, Liliana Teixeira, Béla Török.   

Abstract

A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process leads directly to N-sulfonyl pyrroles, indoles and carbazoles. The selection of appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.

Entities:  

Year:  2007        PMID: 19629194      PMCID: PMC2714272          DOI: 10.1016/j.tetlet.2007.04.021

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  14 in total

1.  Facile Synthesis of 3-Alkylpyrroles.

Authors:  Alexander Zelikin; Venkatram R. Shastri; Robert Langer
Journal:  J Org Chem       Date:  1999-04-30       Impact factor: 4.354

Review 2.  The Pummerer reaction: methodology and strategy for the synthesis of heterocyclic compounds.

Authors:  Scott K Bur; Albert Padwa
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

3.  Versatile direct synthesis of oligosubstituted pyrroles by cycloaddition of alpha-metalated isocyanides to acetylenes.

Authors:  Oleg V Larionov; Armin de Meijere
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-05       Impact factor: 15.336

Review 4.  Simple indole alkaloids and those with a non-rearranged monoterpenoid unit.

Authors:  Masanori Somei; Fumio Yamada
Journal:  Nat Prod Rep       Date:  2005-01-10       Impact factor: 13.423

Review 5.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

6.  Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction.

Authors:  David J Gorin; Nicole R Davis; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

7.  Pd-catalyzed tandem C-N/C-C coupling of gem-dihalovinyl systems: a modular synthesis of 2-substituted indoles.

Authors:  Yuan-Qing Fang; Mark Lautens
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

8.  Organofluorine inhibitors of amyloid fibrillogenesis.

Authors:  Marianna Török; Mohammed Abid; Shilpa C Mhadgut; Béla Török
Journal:  Biochemistry       Date:  2006-04-25       Impact factor: 3.162

9.  Intramolecular C-N bond addition of amides to alkynes using platinum catalyst.

Authors:  Tomohiro Shimada; Itaru Nakamura; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419

10.  Novel ruthenium- and platinum-catalyzed sequential reactions: synthesis of tri- and tetrasubstituted furans and pyrroles from propargylic alcohols and ketones.

Authors:  Yoshiaki Nishibayashi; Masato Yoshikawa; Youichi Inada; Marilyn Daisy Milton; Masanobu Hidai; Sakae Uemura
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-16       Impact factor: 15.336

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