Literature DB >> 19231816

Efficient and regioselective halogenations of 2-amino-1,3-thiazoles with copper salts.

Fabrice G Siméon1, Matthew T Wendahl, Victor W Pike.   

Abstract

Monohalo and dihalo 1,3-thiazole derivatives can be efficiently and selectively prepared under mild conditions from 2-amino-1,3-thiazoles. Halogenations proceed easily in the presence of copper(I) or copper(II) chlorides, bromides, or iodides directly in solution or with supported copper halides.

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Year:  2009        PMID: 19231816      PMCID: PMC2796164          DOI: 10.1021/jo802799c

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


  9 in total

1.  3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]-pyridine: a potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity.

Authors:  Nicholas D P Cosford; Lida Tehrani; Jeffrey Roppe; Edwin Schweiger; Nicholas D Smith; Jeffrey Anderson; Linda Bristow; Jesse Brodkin; Xiaohui Jiang; Ian McDonald; Sara Rao; Mark Washburn; Mark A Varney
Journal:  J Med Chem       Date:  2003-01-16       Impact factor: 7.446

2.  Synthesis and simple 18F-labeling of 3-fluoro-5-(2-(2-(fluoromethyl)thiazol-4-yl)ethynyl)benzonitrile as a high affinity radioligand for imaging monkey brain metabotropic glutamate subtype-5 receptors with positron emission tomography.

Authors:  Fabrice G Siméon; Amira K Brown; Sami S Zoghbi; Velvet M Patterson; Robert B Innis; Victor W Pike
Journal:  J Med Chem       Date:  2007-06-16       Impact factor: 7.446

3.  Radiodefluorination of 3-fluoro-5-(2-(2-[18F](fluoromethyl)-thiazol-4-yl)ethynyl)benzonitrile ([18F]SP203), a radioligand for imaging brain metabotropic glutamate subtype-5 receptors with positron emission tomography, occurs by glutathionylation in rat brain.

Authors:  H Umesha Shetty; Sami S Zoghbi; Fabrice G Siméon; Jeih-San Liow; Amira K Brown; Pavitra Kannan; Robert B Innis; Victor W Pike
Journal:  J Pharmacol Exp Ther       Date:  2008-09-19       Impact factor: 4.030

4.  Synthesis, characterization, and first successful monkey imaging studies of metabotropic glutamate receptor subtype 5 (mGluR5) PET radiotracers.

Authors:  Terence G Hamill; Stephen Krause; Christine Ryan; Celine Bonnefous; Steve Govek; T Jon Seiders; Nicholas D P Cosford; Jeffrey Roppe; Ted Kamenecka; Shil Patel; Raymond E Gibson; Sandra Sanabria; Kerry Riffel; Waisi Eng; Christopher King; Xiaoqing Yang; Mitchell D Green; Stacey S O'Malley; Richard Hargreaves; H Donald Burns
Journal:  Synapse       Date:  2005-06-15       Impact factor: 2.562

5.  Total synthesis of epothilone E and related side-chain modified analogues via a Stille coupling based strategy.

Authors:  K C Nicolaou; N P King; M R Finlay; Y He; F Roschangar; D Vourloumis; H Vallberg; F Sarabia; S Ninkovic; D Hepworth
Journal:  Bioorg Med Chem       Date:  1999-05       Impact factor: 3.641

6.  Synthesis and structure-activity relationships of 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine analogues as potent, noncompetitive metabotropic glutamate receptor subtype 5 antagonists; search for cocaine medications.

Authors:  Yasuyoshi Iso; Ewa Grajkowska; Jarda T Wroblewski; Jared Davis; Nicholas E Goeders; Kenneth M Johnson; Subramaniam Sanker; Bryan L Roth; Werner Tueckmantel; Alan P Kozikowski
Journal:  J Med Chem       Date:  2006-02-09       Impact factor: 7.446

7.  Halogenated 2'-chlorobithiazoles via Pd-catalyzed cross-coupling reactions.

Authors:  Peter Stanetty; Michael Schnürch; Marko D Mihovilovic
Journal:  J Org Chem       Date:  2006-05-12       Impact factor: 4.354

8.  Rapid and mild syntheses of radioiodine-labeled radiopharmaceuticals.

Authors:  G W Kabalka; E E Gooch; K A Sastry
Journal:  J Nucl Med       Date:  1981-10       Impact factor: 10.057

9.  Metabotropic glutamate subtype 5 receptors are quantified in the human brain with a novel radioligand for PET.

Authors:  Amira K Brown; Yasuyuki Kimura; Sami S Zoghbi; Fabrice G Siméon; Jeih-San Liow; William C Kreisl; Andrew Taku; Masahiro Fujita; Victor W Pike; Robert B Innis
Journal:  J Nucl Med       Date:  2008-12       Impact factor: 10.057

  9 in total
  5 in total

1.  The [F]2-Fluoro-1,3-thiazolyl Moiety - an Easily-Accessible Structural Motif for Prospective Molecular Imaging Radiotracers.

Authors:  Fabrice G Siméon; Matthew T Wendahl; Victor W Pike
Journal:  Tetrahedron Lett       Date:  2010-11-17       Impact factor: 2.415

2.  Syntheses of 2-amino and 2-halothiazole derivatives as high-affinity metabotropic glutamate receptor subtype 5 ligands and potential radioligands for in vivo imaging.

Authors:  Fabrice G Siméon; Matthew T Wendahl; Victor W Pike
Journal:  J Med Chem       Date:  2011-01-05       Impact factor: 7.446

3.  Regio- and stereoselective syntheses of the natural product CCR5 antagonist anibamine and its three olefin isomers.

Authors:  Feng Zhang; Saheem Zaidi; Kendra M Haney; Glen E Kellogg; Yan Zhang
Journal:  J Org Chem       Date:  2011-09-13       Impact factor: 4.354

Review 4.  Recent trends in the chemistry of Sandmeyer reaction: a review.

Authors:  Rabia Akhtar; Ameer Fawad Zahoor; Nasir Rasool; Matloob Ahmad; Kulsoom Ghulam Ali
Journal:  Mol Divers       Date:  2021-08-20       Impact factor: 2.943

Review 5.  C-H bond halogenation catalyzed or mediated by copper: an overview.

Authors:  Wenyan Hao; Yunyun Liu
Journal:  Beilstein J Org Chem       Date:  2015-11-09       Impact factor: 2.883

  5 in total

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