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Literature DB >> 20608661

New synthesis of 1-substituted-1H-indazoles via 1,3-dipolar cycloaddition of in situ generated nitrile imines and benzyne.

Christian Spiteri¹, Steve Keeling, John E Moses.

Abstract

A new synthesis of 1-substituted-1H-indazoles via 1,3-dipolar cycloaddition of nitrile imines to benzyne is described. The reaction is completed within 5 min, affording the corresponding N(1)-C(3) disubstituted indazoles in moderate to excellent yields.

Entities: Chemical

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Year: 2010 PMID： 20608661 DOI： 10.1021/ol101150t

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

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Cited

11 in total

1. Synthesis of fused indazole ring systems and application to nigeglanine hydrobromide.

Authors: Aaron C Sather; Orion B Berryman; Julius Rebek
Journal: Org Lett Date: 2012-03-02 Impact factor: 6.005

2. Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes.

Authors: Anton V Dubrovskiy; Richard C Larock
Journal: Org Lett Date: 2011-07-11 Impact factor: 6.005

3. Overturning indolyne regioselectivities and synthesis of indolactam V.

Authors: Sarah M Bronner; Adam E Goetz; Neil K Garg
Journal: J Am Chem Soc Date: 2011-02-25 Impact factor: 15.419

4. Atypical Mode of [3 + 2]-Cycloaddition: Pseudo-1,3-dipole Behavior in Reactions of Electron-Deficient Thioamides with Benzynes.

Authors: Juntian Zhang; Annika C S Page; Vignesh Palani; Junhua Chen; Thomas R Hoye
Journal: Org Lett Date: 2018-08-29 Impact factor: 6.005

5. One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation.

Authors: Nataliya A Markina; Anton V Dubrovskiy; Richard C Larock
Journal: Org Biomol Chem Date: 2012-02-16 Impact factor: 3.876

6. Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.

Authors: Anton V Dubrovskiy; Richard C Larock
Journal: J Org Chem Date: 2012-12-03 Impact factor: 4.354

New synthesis of 1-substituted-1H-indazoles via 1,3-dipolar cycloaddition of in situ generated nitrile imines and benzyne.

1. Synthesis of fused indazole ring systems and application to nigeglanine hydrobromide.

2. Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes.

3. Overturning indolyne regioselectivities and synthesis of indolactam V.

4. Atypical Mode of [3 + 2]-Cycloaddition: Pseudo-1,3-dipole Behavior in Reactions of Electron-Deficient Thioamides with Benzynes.

5. One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation.

6. Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.

7. Synthesis of 1H-Indazoles via Silver(I)-Mediated Intramolecular Oxidative C-H Bond Amination.

8. 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.

Review 9. Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.

10. Metal-free C-C bond formation via coupling of nitrile imines and boronic acids.