Literature DB >> 11112557

A practical synthesis of a COX-2-specific inhibitor.

I W Davies1, J F Marcoux, E G Corley, M Journet, D W Cai, M Palucki, J Wu, R D Larsen, K Rossen, P J Pye, L DiMichele, P Dormer, P J Reider.   

Abstract

A number of synthetic strategies to the Cox-2 specific inhibitor 1 have been described. These studies have led to the identification of a novel pyridine construction using annulation of ketone 2 using a vinamidinium species 29 and ammonia in 97% assay yield. Three approaches to the synthesis of ketone 2 are described that allow for its preparation in large quantities in >65% overall yield from methyl 6-methylnicotinate.

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Year:  2000        PMID: 11112557     DOI: 10.1021/jo000870z

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


  5 in total

1.  An efficient asymmetric synthesis of an estrogen receptor modulator by sulfoxide-directed borane reduction.

Authors:  Zhiguo J Song; Anthony O King; Marjorie S Waters; Fengrui Lang; Daniel Zewge; Matthew Bio; Johnnie L Leazer; Gary Javadi; Amude Kassim; David M Tschaen; Robert A Reamer; Thorsten Rosner; Jennifer R Chilenski; David J Mathre; R P Volante; Richard Tillyer
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-12       Impact factor: 11.205

2.  Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

Authors:  Enxuan Zhang; Jiaze Tang; Suhua Li; Peng Wu; John E Moses; K Barry Sharpless
Journal:  Chemistry       Date:  2016-03-15       Impact factor: 5.236

Review 3.  An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles.

Authors:  Marcus Baumann; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2013-10-30       Impact factor: 2.883

4.  1,2-Diaryl(3-pyridyl)ethanone oximes. Intermolecular hydrogen bonding networks revealed by X-ray diffraction.

Authors:  Ermitas Alcalde; Neus Mesquida; Carmen Alvarez-Rúa; Rosa Cuberes; Jordi Frigola; Santiago García-Granda
Journal:  Molecules       Date:  2008-02-07       Impact factor: 4.411

5.  Application of Vinamidinium Salt Chemistry for a Palladium Free Synthesis of Anti-Malarial MMV048: A "Bottom-Up" Approach.

Authors:  Dinesh J Paymode; Le Chang; Dan Chen; Binglin Wang; Komirishetty Kashinath; Vijayagopal Gopalsamuthiram; D Tyler McQuade; N Vasudevan; Saeed Ahmad; David R Snead
Journal:  Org Lett       Date:  2021-06-29       Impact factor: 6.072

  5 in total

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