Literature DB >> 20092269

Gold- and platinum-catalyzed formal Markownikoff's double hydroamination of alkynes: a rapid access to tetrahydroquinazolinones and angularly-fused analogues thereof.

Nitin T Patil1, Rahul D Kavthe, Vivek S Raut, Valmik S Shinde, Balasubramanian Sridhar.   

Abstract

A highly efficient gold(I)- and platinum(II)-catalyzed process for formal Markownikoff's double hydroamination of alkynes tethered with hydroxyl group has been developed. The method was shown to be applicable to a broad range of 2-aminobenzamides and alkynols leading to the formation of multiply substituted tetrahydroquinazolinones. Interestingly, when Pt(IV)Cl(4) catalyst was employed, cyclic angularly fused compound was obtained.

Entities:  

Year:  2010        PMID: 20092269     DOI: 10.1021/jo902293f

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


  5 in total

1.  Regio- and enantioselective hydroamination of dienes by gold(I)/menthol cooperative catalysis.

Authors:  Osamu Kanno; Wataru Kuriyama; Z Jane Wang; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-07       Impact factor: 15.336

2.  The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones - an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones.

Authors:  Alla I Vaskevych; Nataliia O Savinchuk; Ruslan I Vaskevych; Eduard B Rusanov; Oleksandr O Grygorenko; Mykhailo V Vovk
Journal:  Beilstein J Org Chem       Date:  2021-11-25       Impact factor: 2.883

Review 3.  2,3-Dihydroquinazolin-4(1H)-one as a privileged scaffold in drug design.

Authors:  Mariateresa Badolato; Francesca Aiello; Nouri Neamati
Journal:  RSC Adv       Date:  2018-06-07       Impact factor: 4.036

4.  Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.

Authors:  Jeff P Costello; Eric M Ferreira
Journal:  Org Lett       Date:  2019-12-09       Impact factor: 6.072

5.  Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins.

Authors:  Maddi Sridhar Reddy; Nuligonda Thirupathi; Madala Haribabu
Journal:  Beilstein J Org Chem       Date:  2013-01-28       Impact factor: 2.883

  5 in total

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