Literature DB >> 23268775

Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling.

Huy H Nguyen1, Mark J Kurth.   

Abstract

A variety of N-aryl β-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (μW) assisted intramolecular arene-alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkoxy- and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.

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Year:  2012        PMID： 23268775      PMCID： PMC3549302          DOI： 10.1021/ol303314x

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


  36 in total

1.  Palladium-catalyzed tandem alkenyl and aryl C--N bond formation: a cascade N-annulation route to 1-functionalized indoles.

Authors:  Michael C Willis; Gareth N Brace; Ian P Holmes
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-07       Impact factor: 15.336

2.  Palladium-catalyzed aryl amination-heck cyclization cascade: a one-flask approach to 3-substituted indoles.

Authors:  Thomas Jensen; Henrik Pedersen; Benny Bang-Andersen; Robert Madsen; Morten Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Efficient and versatile synthesis of indoles from enamines and imines by cross-dehydrogenative coupling.

Authors:  Zhuangzhi Shi; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-17       Impact factor: 15.336

4.  Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS).

Authors:  Yang Yang; Yan Zhang; Jianbo Wang
Journal:  Org Lett       Date:  2011-09-14       Impact factor: 6.005

5.  Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: indole synthesis from anilines and ketones.

Authors:  Ye Wei; Indubhusan Deb; Naohiko Yoshikai
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

6.  An expeditious regioselective synthesis of novel bioactive indole-substituted chromene derivatives via one-pot three-component reaction.

Authors:  Roghayeh Hossein nia; Manouchehr Mamaghani; Khalil Tabatabaeian; Farhad Shirini; Mehdi Rassa
Journal:  Bioorg Med Chem Lett       Date:  2012-07-24       Impact factor: 2.823

7.  2,3-Disubstituted indoles via palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with arenediazonium tetrafluoroborates.

Authors:  Sandro Cacchi; Giancarlo Fabrizi; Antonella Goggiamani; Alcide Perboni; Alessio Sferrazza; Paolo Stabile
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

8.  Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides.

Authors:  Benjamin J Stokes; Sheng Liu; Tom G Driver
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

9.  Immobilized alpha-diazophosphonoacetate as a versatile key precursor for palladium catalyzed indole synthesis on a polymer support.

Authors:  Kazuo Yamazaki; Yoshinori Kondo
Journal:  Chem Commun (Camb)       Date:  2002-02-07       Impact factor: 6.222

10.  Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides.

Authors:  Feng Liu; Dawei Ma
Journal:  J Org Chem       Date:  2007-05-27       Impact factor: 4.354
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  4 in total

1.  Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-alkylation/tandem cyclization.

Authors:  Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Tetrahedron Lett       Date:  2015-09-30       Impact factor: 2.415

2.  A chemoselective route to β-enamino esters and thioesters.

Authors:  Dongyue Xin; Kevin Burgess
Journal:  Org Lett       Date:  2014-03-31       Impact factor: 6.005

Review 3.  Benefits and applications of microwave-assisted synthesis of nitrogen containing heterocycles in medicinal chemistry.

Authors:  Maged Henary; Carl Kananda; Laura Rotolo; Brian Savino; Eric A Owens; Giancarlo Cravotto
Journal:  RSC Adv       Date:  2020-04-07       Impact factor: 3.361

4.  An efficient microwave-assisted Suzuki reaction using a new pyridine-pyrazole/Pd(II) species as catalyst in aqueous media.

Authors:  Liqun Shen; Suyu Huang; Yuanmei Nie; Fuhou Lei
Journal:  Molecules       Date:  2013-01-25       Impact factor: 4.411
  4 in total

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