title: Efficient synthesis of 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-2-carboxylic acid derivatives from aniline.
abstract: The first reported synthesis of potential kinase inhibitors, 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-2-carboxylic acid derivatives starting from aniline is described. This efficient high yielding sequence was carried out in six steps without any chromatographic purification. A tandem nucleophilic aromatic substitution/cyclization reaction was used as a key step in the sequence. The versatile intermediate 2-carboxylic acid was used as a suitable precursor to access the functionalization of the C-ring, by convergent analog synthesis of several novel derivatives.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, Mississippi, MS, 38677, USA.
authors.forename: Arindam
authors.initials: A
authors.lastname: Chatterjee
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Cutler
authors.forename: Ikhlas A
authors.initials: IA
authors.lastname: Khan
authors.forename: John S
authors.initials: JS
authors.lastname: Williamson
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry*; D013696:Temperature; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D002264:Carboxylic Acids; D015363:Quinolones; D013876:Thiophenes; C023650:aniline
references.citation: Pharmazie. 2006 Apr;61(4):278-84
references.pmid: 16649537
references.citation: Molecules. 2008 Oct 01;13(10):2442-61
references.pmid: 18830166
references.citation: Bioorg Med Chem. 2009 Jan 15;17(2):523-9
references.pmid: 19101158
references.citation: Org Lett. 2013 Apr 5;15(7):1468-71
references.pmid: 23477600
references.citation: J Med Chem. 2011 Jan 27;54(2):635-54
references.pmid: 21174434
references.citation: Org Lett. 2012 Jun 1;14(11):2838-41
references.pmid: 22621204
references.citation: Bioorg Med Chem. 2010 Apr 15;18(8):2872-9
references.pmid: 20350812
references.citation: Bioorg Med Chem Lett. 2007 Jan 1;17(1):86-93
references.pmid: 17046250
references.citation: Bioorg Med Chem Lett. 2012 May 1;22(9):3327-31
references.pmid: 22460033
references.citation: Bioorg Med Chem. 2012 Sep 15;20(18):5496-506
references.pmid: 22910224