Literature DB >> 17137367

N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation.

Robin B Bedford1, Michael Betham.   

Abstract

N-H carbazoles can be produced from 2-chloroanilines and aryl bromides via consecutive catalytic amination and C-H activation. In many instances, this can be done in a tandem manner in one pot. The methodologies developed can be used in the synthesis of a range of carbazoles, including the natural products Clausine P and glycozolidine and a precursor in the synthesis of Clausines H, K, O, and 7-methoxy-O-methylmukonal, and can be extended to the synthesis of indoles.

Entities:  

Year:  2006        PMID: 17137367     DOI: 10.1021/jo061749g

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  13 in total

1.  Development of a two-step route to 3-PBC and βCCt, two agents active against alcohol self-administration in rodent and primate models.

Authors:  Ojas A Namjoshi; Angelica Gryboski; German O Fonseca; Michael L Van Linn; Zhi-jian Wang; Jeffrey R Deschamps; James M Cook
Journal:  J Org Chem       Date:  2011-05-04       Impact factor: 4.354

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: preparation of carbazoles, indoles, dibenzazepines, and acridines.

Authors:  Dmitry Tsvelikhovsky; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

4.  Enantioselective total synthesis and studies into the configurational stability of bismurrayaquinone A.

Authors:  Leah C Konkol; Fenghai Guo; Amy A Sarjeant; Regan J Thomson
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-07       Impact factor: 15.336

5.  Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

Authors:  W C Peter Tsang; Rachel H Munday; Gordon Brasche; Nan Zheng; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-08-29       Impact factor: 4.354

Review 6.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

7.  Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights.

Authors:  Houng Kang; Madison R Herling; Kyle A Niederer; Young Eun Lee; Peddiahgari Vasu Govardhana Reddy; Sangeeta Dey; Scott E Allen; Paul Sung; Kirsten Hewitt; Carilyn Torruellas; Gina J Kim; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2018-11-14       Impact factor: 4.354

8.  Antibacterial Activity of Murrayaquinone A and 6-Methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione.

Authors:  Biswanath Chakraborty; Suchandra Chakraborty; Chandan Saha
Journal:  Int J Microbiol       Date:  2014-05-20

9.  Construction of highly functionalized carbazoles via condensation of an enolate to a nitro group.

Authors:  Tej Narayan Poudel; Yong Rok Lee
Journal:  Chem Sci       Date:  2015-09-16       Impact factor: 9.825

10.  Fluorescence Sensors Based on Hydroxycarbazole for the Determination of Neurodegeneration-Related Halide Anions.

Authors:  Víctor González-Ruiz; Ángel Cores; M Mar Caja; Vellaisamy Sridharan; Mercedes Villacampa; M Antonia Martín; Ana I Olives; J Carlos Menéndez
Journal:  Biosensors (Basel)       Date:  2022-03-14
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