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Literature DB >> 22337070

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

Nataliya A Markina¹, Anton V Dubrovskiy, Richard C Larock.

Abstract

The reaction of readily accessible 1,1-dialkylhydrazones with commercially available o-(trimethylsilyl)aryl triflates provides a direct one-step route to pharmaceutically important 1-alkylindazoles. The products are obtained in high yields by one-pot NCS-chlorination/aryne annulation or Ac(2)O-acylation/deprotection/aromatization protocols.

Entities: Chemical Disease Species

Mesh：

Substances：
Hydrazones
Indazoles

Year: 2012 PMID： 22337070 PMCID： PMC3764999 DOI： 10.1039/c2ob07117g

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

14 in total

1. Regioselective synthesis of 1-alkyl- or 1-aryl-1H-indazoles via copper-catalyzed cyclizations of 2-haloarylcarbonylic compounds.

Authors: Dolores Viña; Esther del Olmo; José L López-Pérez; Arturo San Feliciano
Journal: Org Lett Date: 2007-02-01 Impact factor: 6.005

2. A phase I and pharmacologic evaluation of the DNA intercalator CI-958 in patients with advanced solid tumors.

Authors: E C Dees; L R Whitfield; W R Grove; S Rummel; L B Grochow; R C Donehower
Journal: Clin Cancer Res Date: 2000-10 Impact factor: 12.531

3. An efficient, facile, and general synthesis of 1h-indazoles by 1,3-dipolar cycloaddition of arynes with diazomethane derivatives.

Authors: Tienan Jin; Yoshinori Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

Authors: Zhijian Liu; Richard C Larock
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

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

Authors: Christian Spiteri; Steve Keeling; John E Moses
Journal: Org Lett Date: 2010-08-06 Impact factor: 6.005

2. 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

2 in total

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

1. Regioselective synthesis of 1-alkyl- or 1-aryl-1H-indazoles via copper-catalyzed cyclizations of 2-haloarylcarbonylic compounds.

2. A phase I and pharmacologic evaluation of the DNA intercalator CI-958 in patients with advanced solid tumors.

3. An efficient, facile, and general synthesis of 1h-indazoles by 1,3-dipolar cycloaddition of arynes with diazomethane derivatives.

4. Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

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

Review 6. Lonidamine: efficacy and safety in clinical trials for the treatment of solid tumors.

7. Indolyne and aryne distortions and nucleophilic regioselectivites.

8. Synthesis of indazoles by the [3+2] cycloaddition of diazo compounds with arynes and subsequent acyl migration.

Review 9. The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles.

10. Radical scavenger activity of bendazac, an anticataract non-steroidal anti-inflammatory agent.

1. Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

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