Literature DB >> 18558759

Synthesis of 1(2H)-isoquinolones by the nickel-catalyzed denitrogenative alkyne insertion of 1,2,3-benzotriazin-4(3H)-ones.

Tomoya Miura1, Motoshi Yamauchi, Masahiro Murakami.   

Abstract

1,2,3-Benzotriazin-4(3H)-ones reacted with internal and terminal alkynes in the presence of a nickel(0)/phosphine catalyst to give a wide range of substituted 1(2H)-isoquinolones in high yield. The reaction proceeded through denitrogenative activation of the triazinone moiety and the following insertion of alkynes.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 18558759     DOI: 10.1021/ol8010826

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


  14 in total

Review 1.  Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems.

Authors:  Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-25       Impact factor: 15.336

2.  Predictable and regioselective insertion of internal unsymmetrical alkynes in rhodium-catalyzed cycloadditions with alkenyl isocyanates.

Authors:  Rebecca Keller Friedman; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

3.  Rh-Catalyzed decarbonylative coupling with alkynes via C-C activation of isatins.

Authors:  Rong Zeng; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2015-01-15       Impact factor: 15.419

Review 4.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

5.  Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes.

Authors:  Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2011-06-21       Impact factor: 6.005

6.  Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

7.  Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

8.  Zinc oxide nanoparticles catalyzed condensation reaction of isocoumarins and 1,7-heptadiamine in the formation of bis-isoquinolinones.

Authors:  Varadhan Krishnakumar; Kesarla Mohan Kumar; Badal Kumar Mandal; Fazlur-Rahman Nawaz Khan
Journal:  ScientificWorldJournal       Date:  2012-03-12

9.  Uncovering the importance of proton donors in TmI2-promoted electron transfer: facile C-N bond cleavage in unactivated amides.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-12       Impact factor: 15.336

10.  Nickel-catalyzed C-O/N-H, C-S/N-H, and C-CN/N-H annulation of aromatic amides with alkynes: C-O, C-S, and C-CN activation.

Authors:  Yasuaki Iyori; Rina Ueno; Aoi Morishige; Naoto Chatani
Journal:  Chem Sci       Date:  2020-12-09       Impact factor: 9.825

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.