Synthesis of 3-Hydroxy-4-Substituted Picolinonitriles from 4-Propargylaminoisoxazoles via Stepwise and One-Pot Isoxazolopyridine Formation/N–O Bond Cleavage Sequence

A unique synthetic approach to 3-hydroxy-4-substituted picolinonitriles is achieved via gold(I)-catalyzed cyclization of 4-propargylaminoisoxazoles and subsequent N–O bond cleavage of isoxazolopyridines under mild reaction conditions in a stepwise and one-pot fashion.

[1]  Shinichiro Fuse,et al.  Gold(I)-Catalyzed Intramolecular SEAr Reaction: Efficient Synthesis of Isoxazole-Containing Fused Heterocycles. , 2018, Organic letters.

[2]  P. Subramaniam,et al.  Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones , 2017 .

[3]  Shinichiro Fuse,et al.  Step-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C–H Direct Arylations , 2017, Synthesis.

[4]  Shinichiro Fuse,et al.  Generation of an 4-Isoxazolyl Anion Species: Facile Access to Multifunctionalized Isoxazoles. , 2016, Angewandte Chemie.

[5]  Zhinan Jin,et al.  Synthesis and Anti-Influenza Activity of Pyridine, Pyridazine, and Pyrimidine C-Nucleosides as Favipiravir (T-705) Analogues. , 2016, Journal of medicinal chemistry.

[6]  P. Beuning,et al.  Progress against Escherichia coli with the Oxazolidinone Class of Antibacterials: Test Case for a General Approach To Improving Whole-Cell Gram-Negative Activity. , 2016, ACS infectious diseases.

[7]  Jean Martínez,et al.  Comprehensive study of the organic-solvent-free CDI-mediated acylation of various nucleophiles by mechanochemistry. , 2015, Chemistry.

[8]  M. Szostak,et al.  Recent Developments in the Synthesis and Reactivity of Isoxazoles: Metal Catalysis and Beyond , 2015 .

[9]  M. McVean,et al.  Discovery of 2-pyridylureas as glucokinase activators. , 2014, Journal of medicinal chemistry.

[10]  P. Renard,et al.  Design, synthesis and biological evaluation of novel tetrahydroacridine pyridine- aldoxime and -amidoxime hybrids as efficient uncharged reactivators of nerve agent-inhibited human acetylcholinesterase. , 2014, European journal of medicinal chemistry.

[11]  H. Omar,et al.  Design, synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity. , 2013, Bioorganic & medicinal chemistry.

[12]  Jean Martínez,et al.  Mechanosynthesis of amides in the total absence of organic solvent from reaction to product recovery. , 2012, Chemical communications.

[13]  P. Renard,et al.  Design, Synthesis and Evaluation of New α‐Nucleophiles for the Hydrolysis of Organophosphorus Nerve Agents: Application to the Reactivation of Phosphorylated Acetylcholinesterase. , 2011 .

[14]  G. McGaughey,et al.  Design and synthesis of pyridone inhibitors of non-nucleoside reverse transcriptase. , 2011, Bioorganic & medicinal chemistry letters.

[15]  P. Renard,et al.  Design, synthesis and evaluation of new α-nucleophiles for the hydrolysis of organophosphorus nerve agents: application to the reactivation of phosphorylated acetylcholinesterase , 2011 .

[16]  S. Rault,et al.  Straightforward Access to Ethyl 3‐Aminofuropyridine‐2‐carboxylates from 1‐Chloro‐2‐cyano‐ or 1‐Hydroxy‐2‐cyano‐Substituted Pyridines. , 2008 .

[17]  Fujita,et al.  Novel Antifungal Antibiotics from Streptomyces sp . 517-02 VIII . Reactive Oxygen Species Generated by C 9-UK-2 A , a Derivative of UK-2 A , in Rhodotorula mucilaginosa , 2008 .

[18]  S. Rault,et al.  Straightforward access to ethyl 3-aminofuropyridine-2-carboxylates from 1-chloro-2-cyano-or 1 -hydroxy -2 -cyano -substituted pyridines , 2007 .

[19]  Keiichi,et al.  UK-2 A , B , C and D , Novel Antifungal Antibiotics from Streptomyces sp . 517-02 I . Fermentation , Isolation , and Biological Properties , 2006 .

[20]  M. Bock,et al.  Tetrabutylammonium salt induced denitration of nitropyridines: synthesis of fluoro-, hydroxy-, and methoxypyridines. , 2005, Organic letters.

[21]  L. Subramanian.  Introduction of the cyano group by substitution of a halogen , 2005 .

[22]  T. Maekawa,et al.  Synthesis and Biological Activity of Novel 2-(α-Alkoxyimino)benzylpyridine Derivatives as K+ Channel Openers. , 1998 .

[23]  S. Yamamoto,et al.  Synthesis and biological activity of novel 2-(alpha-alkoxyimino)benzylpyridine derivatives as K+ channel openers. , 1997, Chemical & pharmaceutical bulletin.

[24]  M. Ueki,et al.  UK-2A, B, C and D, novel antifungal antibiotics from Streptomyces sp. 517-02. II. Structural elucidation. , 1996, The Journal of antibiotics.

[25]  M. Ueki,et al.  UK-2A, B, C and D, novel antifungal antibiotics from Streptomyces sp. 517-02. I. Fermentation, isolation, and biological properties. , 1996, The Journal of antibiotics.

[26]  Donald Hilvert,et al.  Transition State of the Base-Promoted Ring-Opening of Isoxazoles. Theoretical Prediction of Catalytic Functionalities and Design of Haptens for Antibody Production , 1996 .

[27]  J. Frei,et al.  Evaluation of desferrithiocin and its synthetic analogues as orally effective iron chelators. , 1991, Journal of medicinal chemistry.

[28]  Y. Goto,et al.  Facile synthesis of some oxazolopyridines and their N-oxides via intramolecular cyclization , 1987 .

[29]  F. Lucchesini,et al.  On the base catalysed ring opening of 3-unsubstituted isoxazoles. Derivatives of 4- and 5-phenylisoxazole , 1977 .

[30]  J. B. Petersen,et al.  Preparation of Derivatives of 3-Hydroxypicolinic Acid from Furfural. , 1965 .