title: Modular o-quinone catalyst system for dehydrogenation of tetrahydroquinolines under ambient conditions.
abstract: Quinolines are common pharmacophores present in numerous FDA-approved pharmaceuticals and other bioactive compounds. Here, we report the design and development of new o-quinone-based catalysts for the oxidative dehydrogenation of tetrahydroquinolines to afford quinolines. Use of a Co(salophen) cocatalyst allows the reaction to proceed efficiently with ambient air at room temperature. The utility of the catalytic method is demonstrated in the preparation of a number of medicinally relevant quinolines.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Alison E
authors.initials: AE
authors.lastname: Wendlandt
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
mesh_terms: D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D006865:Hydrogenation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011804:Quinolines / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013997:Time Factors
chemical_list: D056831:Coordination Complexes; D011804:Quinolines; D011809:Quinones; D012428:Ruthenium; C542964:1,2,3,4-tetrahydroquinoline
references.citation: J Med Chem. 2013 Oct 24;56(20):8073-88
references.pmid: 24090311
references.citation: J Am Chem Soc. 2013 Feb 20;135(7):2419-22
references.pmid: 23350926
references.citation: J Am Chem Soc. 2014 Jun 18;136(24):8564-7
references.pmid: 24877556
references.citation: Inorg Chem. 1986 Mar 1;25(7):1072
references.pmid: 23240930
references.citation: Angew Chem Int Ed Engl. 2008;47(19):3506-23
references.pmid: 18383499
references.citation: Org Lett. 2012 Jun 1;14(11):2850-3
references.pmid: 22594886
references.citation: J Am Chem Soc. 2014 Jan 8;136(1):506-12
references.pmid: 24328193
references.citation: Org Biomol Chem. 2010 May 7;8(9):2180-97
references.pmid: 20401395
references.citation: Angew Chem Int Ed Engl. 2013 Jul 1;52(27):6983-7
references.pmid: 23686696
references.citation: Angew Chem Int Ed Engl. 2013 Dec 23;52(52):14209-13
references.pmid: 24353239
references.citation: Biol Pharm Bull. 2007 Oct;30(10):1923-9
references.pmid: 17917263
references.citation: Acc Chem Res. 2004 Feb;37(2):131-9
references.pmid: 14967060
references.citation: J Biol Chem. 1996 Nov 1;271(44):27189-92
references.pmid: 8910283
references.citation: Org Biomol Chem. 2010 Dec 21;8(24):5661-73
references.pmid: 20927480
references.citation: J Am Chem Soc. 2012 Oct 31;134(43):18022-33
references.pmid: 23046387
references.citation: Angew Chem Int Ed Engl. 2012 May 29;51(22):5409-12
references.pmid: 22499249
references.citation: Bioorg Med Chem Lett. 2013 May 1;23(9):2750-8
references.pmid: 23518280
references.citation: Science. 2013 Jan 4;339(6115):43-4
references.pmid: 23288531
references.citation: Jpn J Cancer Res. 1997 Oct;88(10):992-1002
references.pmid: 9414662
references.citation: J Am Chem Soc. 2009 Jun 24;131(24):8410-2
references.pmid: 19480425
references.citation: Eur J Med Chem. 2011 Apr;46(4):1306-24
references.pmid: 21334792
references.citation: Angew Chem Int Ed Engl. 2003 Apr 4;42(13):1479-83
references.pmid: 12698478
references.citation: Dalton Trans. 2013 Oct 7;42(37):13305-7
references.pmid: 23925310