Literature DB >> 21753857

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

Fei Liu1, Todd Evans, Bhaskar C Das.   

Abstract

2H-Chromenes were synthesized from salicylaldehyde using potassium vinylic borates in the presence of secondary amines. We synthesized these 2H-chromene derivatives as a part of an ongoing project to develop inhibitors for TGF-β receptors. Potassium vinyl trifluoroborates react with salicylaldehydes at 80 °C in the presence of a secondary amine and produced 2-substituted 2H-chromene derivatives with a 70-90% yield.

Entities:  

Year:  2008        PMID: 21753857      PMCID: PMC3132890          DOI: 10.1016/j.tetlet.2008.01.008

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  26 in total

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Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-02       Impact factor: 15.336

2.  A Highly Efficient and Practical Synthesis of Chromene Derivatives Using Ring-Closing Olefin Metathesis.

Authors:  Sukbok Chang; Robert H. Grubbs
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

3.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

4.  Synthesis and pharmacological properties of nebivolol, a new antihypertensive compound.

Authors:  G Van Lommen; M De Bruyn; M Schroven
Journal:  J Pharm Belg       Date:  1990 Nov-Dec

5.  Why drinking green tea could prevent cancer.

Authors:  J Jankun; S H Selman; R Swiercz; E Skrzypczak-Jankun
Journal:  Nature       Date:  1997-06-05       Impact factor: 49.962

6.  Electrocyclic ring closure of the enols of vinyl quinones. A 2H-chromene synthesis.

Authors:  K A Parker; T L Mindt
Journal:  Org Lett       Date:  2001-11-29       Impact factor: 6.005

7.  2H-Chromenes from salicylaldehydes by a catalytic petasis reaction

Authors: 
Journal:  Org Lett       Date:  2000-12-14       Impact factor: 6.005

8.  Oxidation of hydroxyl-substituted organotrifluoroborates.

Authors:  Gary A Molander; Daniel E Petrillo
Journal:  J Am Chem Soc       Date:  2006-08-02       Impact factor: 15.419

9.  3-Methyl-2H-1-benzopyran potassium channel activators.

Authors:  R Gericke; J Harting; I Lues; C Schittenhelm
Journal:  J Med Chem       Date:  1991-10       Impact factor: 7.446

10.  Synthesis and antihypertensive activity of 4-(1,2-dihydro-2-oxo-1-pyridyl)-2H-1-benzopyrans and related compounds, new potassium channel activators.

Authors:  R Bergmann; R Gericke
Journal:  J Med Chem       Date:  1990-02       Impact factor: 7.446

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  10 in total

1.  Synthesis of substituted 2H-chromenes by a three-component reaction as potential antioxidants.

Authors:  Chitreddy V Subbareddy; Radhakrishnan Subashini; Shanmugam Sumathi
Journal:  Mol Divers       Date:  2017-06-20       Impact factor: 2.943

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, Intramolecular Sulfenofunctionalization of Alkenes with Phenols.

Authors:  Scott E Denmark; David J P Kornfilt
Journal:  J Org Chem       Date:  2017-03-03       Impact factor: 4.354

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.  Synthesis of a boron-containing amidoxime reagent and its application to synthesize functionalized oxadiazole and quinazolinone derivatives.

Authors:  Bhaskar C Das; Nitesh K Nandwana; Devi P Ojha; Sasmita Das; Todd Evans
Journal:  Tetrahedron Lett       Date:  2022-01-25       Impact factor: 2.032

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.  Design and synthesis of 3,5-disubstituted boron-containing 1,2,4-oxadiazoles as potential combretastatin A-4 (CA-4) analogs.

Authors:  Bhaskar C Das; Xiang-Ying Tang; Patrick Rogler; Todd Evans
Journal:  Tetrahedron Lett       Date:  2012-08-01       Impact factor: 2.415

8.  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

9.  Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues.

Authors:  Bhaskar C Das; Sakkarapalayam M Mahalingam; Todd Evans
Journal:  Tetrahedron Lett       Date:  2009-06-24       Impact factor: 2.415

10.  Kinetic resolution in asymmetric epoxidation using iminium salt catalysis.

Authors:  Philip C Bulman Page; Louise F Appleby; Yohan Chan; David P Day; Benjamin R Buckley; Alexandra M Z Slawin; Steven M Allin; Michael J McKenzie
Journal:  J Org Chem       Date:  2013-08-06       Impact factor: 4.354

  10 in total

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