Literature DB >> 22852549

Allylic amination and N-arylation-based domino reactions providing rapid three-component strategies to fused pyrroles with different substituted patterns.

Bo Jiang1, Ying Li, Man-Su Tu, Shu-Liang Wang, Shu-Jiang Tu, Guigen Li.   

Abstract

New three-n class="Chemical">component domino reaction providing divergent approaches to multifunctionalized fused pyrroles with different substituted patterns have been established (40 examples). The direct C(sp(3))-N bond formation was achieved through intermolecular allylic amination in a one-pot operation, and N-arylation of amines was realized by varying N-amino acid enaminones. The reaction is easy to perform simply by mixing three common reactants in acetic acid under microwave heating. The reaction proceeds at fast rates and can be finished within 30 min, which makes workup convenient to give good chemical yields.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22852549      PMCID: PMC3442375          DOI: 10.1021/jo301323r

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


  71 in total

1.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Pyrrole syntheses by multicomponent coupling reactions.

Authors:  Geneviève Balme
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-26       Impact factor: 15.336

3.  Recent advances in catalytic intramolecular C-H aminations.

Authors:  Huw M L Davies; Matthew S Long
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-06       Impact factor: 15.336

Review 4.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

5.  Dirhodium tetracarboxylates derived from adamantylglycine as chiral catalysts for enantioselective C-h aminations.

Authors:  Ravisekhara P Reddy; Huw M L Davies
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

6.  Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.

Authors:  Dawei Ma; Qian Cai
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

7.  Synthesis of heterocycles from alkyl 3-(dimethylamino)propenoates and related enaminones.

Authors:  Branko Stanovnik; Jurij Svete
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

8.  Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Authors:  Chungen Liang; Florence Collet; Fabien Robert-Peillard; Paul Müller; Robert H Dodd; Philippe Dauban
Journal:  J Am Chem Soc       Date:  2007-12-12       Impact factor: 15.419

9.  Intramolecular C-N bond formation reactions catalyzed by ruthenium porphyrins: amidation of sulfamate esters and aziridination of unsaturated sulfonamides.

Authors:  Jiang-Lin Liang; Shi-Xue Yuan; Jie-Sheng Huang; Chi-Ming Che
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

10.  The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.

Authors:  Lutz F Tietze; Tom Kinzel; C Christian Brazel
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

View more
  3 in total

1.  Synthesis of enaminones and their difluoroboron complexes through domino aryl migration.

Authors:  Zheng Yang; Bo Jiang; Wen-Juan Hao; Peng Zhou; Shu-Jiang Tu; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

2.  Divergent synthesis of dual 1,4-dihydropyridines with different substituted patterns from enaminones and aldehydes through domino reactions.

Authors:  Fu-Jun Liu; Tian-Tian Sun; Yun-Gang Yang; Chao Huang; Xue-Bing Chen
Journal:  RSC Adv       Date:  2018-04-03       Impact factor: 3.361

3.  Domino reaction of arylglyoxals with pyrazol-5-amines: selective access to pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles.

Authors:  Bo Jiang; Wei Fan; Mu-Yan Sun; Qin Ye; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  J Org Chem       Date:  2014-05-22       Impact factor: 4.354

  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.