Literature DB >> 29850673

Transition-metal-free C-H amidation and chlorination: synthesis of N/N'-mono-substituted imidazopyridin-2-ones from N-pyridyl-N-hydroxylamine intermediates.

Katarzyna N Lee1, Dominique N Spiegowski, Johnny W Lee, Sanghyun Lim, Fuhua Zhao, Ming-Yu Ngai.   

Abstract

Non-symmetric 1,3-substituted imidazopyridin-2-ones are a common structural scaffold found among many biologically active molecules. Herein we report an efficient, mild, and transition-metal free C-H amidation strategy to access such a pyrido-fused cyclic urea framework in good yields and with a broad functional group tolerance.

Entities:  

Year:  2018        PMID: 29850673      PMCID: PMC6029925          DOI: 10.1039/c8cc02425a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  15 in total

1.  Practical way to imidazo[4,5-b] and [4,5-c]pyridine-2-ones via cascade ureidation/palladium-catalyzed cyclization.

Authors:  Franck Lach; Patrice Koza
Journal:  ACS Comb Sci       Date:  2012-08-10       Impact factor: 3.784

2.  Rearrangement of N-oxyenamines and related reactions.

Authors:  Andrey A Tabolin; Sema L Ioffe
Journal:  Chem Rev       Date:  2014-03-14       Impact factor: 60.622

3.  Structure guided development of novel thymidine mimetics targeting Pseudomonas aeruginosa thymidylate kinase: from hit to lead generation.

Authors:  Jun Yong Choi; Mark S Plummer; Jeremy Starr; Charlene R Desbonnet; Holly Soutter; Jeanne Chang; J Richard Miller; Keith Dillman; Alita A Miller; William R Roush
Journal:  J Med Chem       Date:  2012-01-13       Impact factor: 7.446

4.  Efficient access to cyclic ureas via Pd-catalyzed cyclization.

Authors:  Mark McLaughlin; Michael Palucki; Ian W Davies
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

5.  Synthesis and analgesic activity of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-b]pyridin-2-ones and 3-(substituted phenyl)-1,2,3-triazolo[4,5-b]pyridines.

Authors:  R L Clark; A A Pessolano; T Y Shen; D P Jacobus; H Jones; V J Lotti; L M Flataker
Journal:  J Med Chem       Date:  1978-09       Impact factor: 7.446

6.  Synthesis and biological properties of pyrido [2, 3-d] pyridazine derivatives.

Authors:  L Kuczyński; A Mrozikiewicz; W Banaszkiewicz; S Respond
Journal:  Pol J Pharmacol Pharm       Date:  1982

7.  Synthesis of disubstituted imidazo[4,5-b]pyridin-2-ones.

Authors:  Jeffrey T Kuethe; Audrey Wong; Ian W Davies
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

8.  Identification of potent, noncovalent fatty acid amide hydrolase (FAAH) inhibitors.

Authors:  Darin J Gustin; Zhihua Ma; Xiaoshan Min; Yihong Li; Christine Hedberg; Cris Guimaraes; Amy C Porter; Michelle Lindstrom; Dianna Lester-Zeiner; Guifen Xu; Timothy J Carlson; Shouhua Xiao; Cesar Meleza; Richard Connors; Zhulun Wang; Frank Kayser
Journal:  Bioorg Med Chem Lett       Date:  2011-02-17       Impact factor: 2.823

Review 9.  Calcitonin gene-related peptide receptor antagonists: new therapeutic agents for migraine.

Authors:  Ian M Bell
Journal:  J Med Chem       Date:  2014-06-24       Impact factor: 7.446

10.  Selective C-O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenes.

Authors:  Johnny W Lee; Dominique N Spiegowski; Ming-Yu Ngai
Journal:  Chem Sci       Date:  2017-06-05       Impact factor: 9.825

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