Literature DB >> 15901172

Synthesis of carbazoles from ynamides by intramolecular dehydro Diels-Alder reactions.

María Fernanda Martínez-Esperón1, David Rodríguez, Luis Castedo, Carlos Saá.   

Abstract

[reaction: see text]. A new approach to carbazoles and benzannulated carbazoles by means of intramolecular dehydro Diels-Alder reactions of ynamides is reported. By using this approach, carbazoles and benzo[b]-, tetrahydrobenzo[b]-, naphtho[1,2-b]-, naphtho[2,1-b]-, and dibenzo[a,c]carbazoles have been prepared in moderate-to-good yields.

Entities:  

Year:  2005        PMID: 15901172     DOI: 10.1021/ol050609a

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


  10 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  Intramolecular [4 + 2] cycloadditions of benzynes with conjugated enynes, arenynes, and dienes.

Authors:  Martin E Hayes; Hiroshi Shinokubo; Rick L Danheiser
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

Review 3.  Chemistry of polyvalent iodine.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

4.  Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family.

Authors:  Tao Wang; Thomas R Hoye
Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419

5.  SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE.

Authors:  Amanda L Kohnen; Joshua R Dunetz; Rick L Danheiser
Journal:  Organic Synth       Date:  2007

6.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

7.  Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Chem Commun (Camb)       Date:  2014-02-12       Impact factor: 6.222

8.  Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-25       Impact factor: 15.336

9.  Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Authors:  Peng Zhang; Andrea M Cook; Yang Liu; Christian Wolf
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354

10.  Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C-H Aminations.

Authors:  Xianhai Tian; Lina Song; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-02       Impact factor: 15.336

  10 in total

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