Literature DB >> 20394430

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

Chunrui Wu1, Yuesi Fang, Richard C Larock, Feng Shi.   

Abstract

A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.

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Year:  2010        PMID： 20394430      PMCID： PMC2871071          DOI： 10.1021/ol100586r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  29 in total

1.  A general and mild palladium-catalyzed domino reaction for the synthesis of 2H-indazoles.

Authors:  Nis Halland; Marc Nazaré; Omar R'kyek; Jorge Alonso; Matthias Urmann; Andreas Lindenschmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne.

Authors:  Christian Spiteri; Pallavi Sharma; Fengzhi Zhang; Simon J F Macdonald; Steve Keeling; John E Moses
Journal:  Chem Commun (Camb)       Date:  2010-01-11       Impact factor: 6.222

3.  Antiinflammatory sydnones. 1.

Authors:  H Wagner; J B Hill
Journal:  J Med Chem       Date:  1974-12       Impact factor: 7.446

4.  Influence of the aliphatic spacer length on the 5-HT1A receptor activity of new arylpiperazines with an indazole system.

Authors:  M H Paluchowska; B Duszyńska; A Kłodzińska; E Tatarczyńska
Journal:  Pol J Pharmacol       Date:  2000 May-Jun

5.  Synthesis of benzisoxazoles by the [3 + 2] cycloaddition of in situ generated nitrile oxides and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

6.  New pyrazole alkaloids from the root bark of Newbouldia laevis.

Authors:  A J Aladesanmi; R Nia; A Nahrstedt
Journal:  Planta Med       Date:  1998-02       Impact factor: 3.352

7.  A novel synthesis of 2-aryl-2H-indazoles via a palladium-catalyzed intramolecular amination reaction.

Authors:  J J Song; N K Yee
Journal:  Org Lett       Date:  2000-02-24       Impact factor: 6.005

8.  Preparation of polyfunctional indazoles and heteroarylazo compounds using highly functionalized zinc reagents.

Authors:  Benjamin Haag; Zhihua Peng; Paul Knochel
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

9.  Indazoles: regioselective protection and subsequent amine coupling reactions.

Authors:  David J Slade; Nicholas F Pelz; Wanda Bodnar; John W Lampe; Paul S Watson
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

10.  Convenient access to 1,3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation.

Authors:  N Satheesha Rai; Balakrishna Kalluraya; B Lingappa; Shaliny Shenoy; Vedavati G Puranic
Journal:  Eur J Med Chem       Date:  2007-08-30       Impact factor: 6.514
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  12 in total

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

Authors:  Expédite Yen-Pon; Pier Alexandre Champagne; Lucie Plougastel; Sandra Gabillet; Pierre Thuéry; Mizuki Johnson; Gilles Muller; Grégory Pieters; Frédéric Taran; K N Houk; Davide Audisio
Journal:  J Am Chem Soc       Date:  2019-01-15       Impact factor: 15.419

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

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

3.  Facile syntheses of novel benzo-1,3-dioxolo-, benzothiazolo-, pyrido-, and quinolino-fused 5H-benzo[d]-pyrazolo[5,1-b][1,3]-oxazines and 1H-pyrazoles.

Authors:  Belem Avila; Danielle M Solano; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2011-02-04       Impact factor: 6.005

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

Authors:  Yuesi Fang; Chunrui Wu; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2011-10-12       Impact factor: 4.354

5.  Synthesis of pyrido[1,2-a]indole malonates and amines through aryne annulation.

Authors:  Donald C Rogness; Nataliya A Markina; Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2012-03-06       Impact factor: 4.354

6.  Palladium(0)-catalyzed aryne annulation: a powerful strategy for the synthesis of thio-bridged compounds.

Authors:  Mayur I Morja; Kishor H Chikhalia
Journal:  Mol Divers       Date:  2022-04-22       Impact factor: 2.943

7.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

8.  Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones.

Authors:  Yuesi Fang; Richard C Larock
Journal:  Tetrahedron       Date:  2012-02-09       Impact factor: 2.457

9.  Acid and base catalyzed Davis-Beirut reaction: experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles.

Authors:  Belem Avila; Mohammad H El-Dakdouki; Musa Z Nazer; Jason G Harrison; Dean J Tantillo; Makhluf J Haddadin; Mark J Kurth
Journal:  Tetrahedron Lett       Date:  2012-09-15       Impact factor: 2.415

10.  2,2'-(Propane-1,3-di-yl)bis-(2H-indazole).

Authors:  Saúl Ovalle; Sylvain Bernès; Nancy Pérez Rodríguez; Perla Elizondo Martínez
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-30
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