Literature DB >> 11112644

2H-Chromenes from salicylaldehydes by a catalytic petasis reaction

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Abstract

The Petasis condensation of vinylic or aromatic boronic acids, aromatic aldehydes, and amines is assisted by a hydroxy group adjacent to the aldehyde moiety. The products derived from salicylaldehydes and vinylboronic acids undergo cyclization to 2H-chromene compounds with ejection of amine upon heating. A catalytic preparation of 2H-chromenes using resin-bound amine is reported, allowing the convenient incorporation of a variety of components.

Entities:  

Year:  2000        PMID: 11112644     DOI: 10.1021/ol006710r

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


  16 in total

1.  Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates.

Authors:  Fei Liu; Todd Evans; Bhaskar C Das
Journal:  Tetrahedron Lett       Date:  2008-03-03       Impact factor: 2.415

2.  Metalloradical approach to 2H-chromenes.

Authors:  Nanda D Paul; Sutanuva Mandal; Matthias Otte; Xin Cui; X Peter Zhang; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2014-01-08       Impact factor: 15.419

3.  Catalytic enantioselective synthesis of 2-aryl-chromenes.

Authors:  Bi-Shun Zeng; Xinyi Yu; Paul W Siu; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-06       Impact factor: 9.825

4.  Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade.

Authors:  Nilanjana Majumdar; Keith A Korthals; William D Wulff
Journal:  J Am Chem Soc       Date:  2011-12-16       Impact factor: 15.419

5.  Asymmetric petasis reactions catalyzed by chiral biphenols.

Authors:  Sha Lou; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2008-05-07       Impact factor: 15.419

6.  A forward chemical screen using zebrafish embryos with novel 2-substituted 2H-chromene derivatives.

Authors:  Ingrid Torregroza; Todd Evans; Bhaskar C Das
Journal:  Chem Biol Drug Des       Date:  2009-03       Impact factor: 2.817

7.  Phosphinite- and phosphite-based Type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines.

Authors:  Ping He; Yong Lu; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2007-07-23       Impact factor: 2.415

8.  Synthesis of chromeno[3,4-B]quinoline derivatives by heterogeneous [Cu(II)BHPPDAH] catalyst without being immobilized on any support under mild conditions using PEG 300 as green solvent.

Authors:  Hashem Sharghi; Reza Khalifeh; Zahra Rashidi
Journal:  Mol Divers       Date:  2013-08-22       Impact factor: 2.943

9.  Synthesis of 2H-chromenes and 1,2-dihydroquinolines from aryl aldehydes, amines, and alkenylboron compounds.

Authors:  Nicos A Petasis; Alexey Butkevich
Journal:  J Organomet Chem       Date:  2009-05-01       Impact factor: 2.369

10.  Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives.

Authors:  Ishmael B Masesane; Zelalem Yibralign Desta
Journal:  Beilstein J Org Chem       Date:  2012-12-12       Impact factor: 2.883

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