Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

Literature DB >> 30628450

Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

Expédite Yen-Pon¹, Pier Alexandre Champagne², Lucie Plougastel¹, Sandra Gabillet¹, Pierre Thuéry³, Mizuki Johnson⁴, Gilles Muller⁴, Grégory Pieters¹, Frédéric Taran¹, K N Houk², Davide Audisio¹.

Abstract

The first approach to pyrazole-containing helicenes via sydnone-aryne [3 + 2]-cycloaddition is described. An unprecedented regioselectivity in the cycloaddition step toward the more sterically constrained product was observed in the presence of extended aromatic scaffolds. DFT calculations enabled understanding the origin of this unexpected selectivity.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2019 PMID： 30628450 PMCID： PMC7075354 DOI： 10.1021/jacs.8b11465

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

43 in total

1. Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: a potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines.

Authors: Jingjing Zhao; Pan Li; Chunrui Wu; Hongli Chen; Wenying Ai; Renhong Sun; Hailong Ren; Richard C Larock; Feng Shi
Journal: Org Biomol Chem Date: 2012-01-25 Impact factor: 3.876

2. Helical chiral pyridine N-oxides: a new family of asymmetric catalysts.

Authors: Norito Takenaka; Robindro Singh Sarangthem; Burjor Captain
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Physicochemical and Electronic Properties of Cationic [6]Helicenes: from Chemical and Electrochemical Stabilities to Far-Red (Polarized) Luminescence.

Authors: Johann Bosson; Geraldine M Labrador; Simon Pascal; François-Alexandre Miannay; Oleksandr Yushchenko; Haidong Li; Laurent Bouffier; Neso Sojic; Roberto C Tovar; Gilles Muller; Denis Jacquemin; Adèle D Laurent; Boris Le Guennic; Eric Vauthey; Jérôme Lacour
Journal: Chemistry Date: 2016-11-25 Impact factor: 5.236

Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

1. Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: a potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines.

2. Helical chiral pyridine N-oxides: a new family of asymmetric catalysts.

3. Physicochemical and Electronic Properties of Cationic [6]Helicenes: from Chemical and Electrochemical Stabilities to Far-Red (Polarized) Luminescence.

4. Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

5. 2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors.

6. Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

7. Enantioselective Synthesis of [6]Carbohelicenes.

8. Indolyne and aryne distortions and nucleophilic regioselectivites.

9. One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes.

10. Intermolecular oxidative annulation of 2-aminoanthracenes to diazaacenes and aza[7]helicenes.

1. Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans.

2. One-step synthesis of benzo[b]thiophenes by aryne reaction with alkynyl sulfides.