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Literature DB >> 21744843

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

Abstract

A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones and acridones has been developed starting from readily available 1,1-dimethylhydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2011 PMID： 21744843 PMCID： PMC3153441 DOI： 10.1021/ol2016803

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

19 in total

1. Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa.

Authors: Alain F Kamdem Waffo; Philip H Coombes; Neil R Crouch; Dulcie A Mulholland; Sawsan M M El Amin; Peter J Smith
Journal: Phytochemistry Date: 2006-12-15 Impact factor: 4.072

2. Acridone derivatives are selective inhibitors of HIV-1 replication in chronically infected cells.

Authors: M Fujiwara; M Okamoto; M Okamoto; M Watanabe; H Machida; S Shigeta; K Konno; T Yokota; M Baba
Journal: Antiviral Res Date: 1999-10 Impact factor: 5.970

3. CO2 incorporation reaction using arynes: straightforward access to benzoxazinone.

Authors: Hiroto Yoshida; Hiroyuki Fukushima; Joji Ohshita; Atsutaka Kunai
Journal: J Am Chem Soc Date: 2006-08-30 Impact factor: 15.419

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. Direct C-arylation of beta-enamino esters and ketones with arynes.

Authors: Yeeman K Ramtohul; Anik Chartrand
Journal: Org Lett Date: 2007-02-20 Impact factor: 6.005

6. 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

4. 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

4 in total

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

1. Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa.

2. Acridone derivatives are selective inhibitors of HIV-1 replication in chronically infected cells.

3. CO2 incorporation reaction using arynes: straightforward access to benzoxazinone.

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

5. Direct C-arylation of beta-enamino esters and ketones with arynes.

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

7. Rapid synthesis of the indole-indolone scaffold via [3+2] annulation of arynes by methyl indole-2-carboxylates.

8. Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides.

9. In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum.

Review 10. Design of novel antitumor DNA alkylating agents: the benzacronycine series.

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

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

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

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