title: Oxidative dehydrogenative couplings of pyrazol-5-amines selectively forming azopyrroles.
abstract: New oxidative dehydrogenative couplings of pyrazol-5-amines for the selective synthesis of azopyrrole derivatives have been described. The former reaction simultaneously installs C-I and N-N bonds through iodination and oxidation, whereas the latter involved a copper-catalyzed oxidative coupling process. The resulting iodo-substituted azopyrroles were employed by treatment with various terminal alkynes through Sonogashira cross-coupling leading to new azo compounds.
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
authors.forename: Bo
authors.initials: B
authors.lastname: Jiang
authors.forename: Yi
authors.initials: Y
authors.lastname: Ning
authors.forename: Wei
authors.initials: W
authors.lastname: Fan
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D001391:Azo Compounds; D011720:Pyrazoles
references.citation: J Am Chem Soc. 1965 Apr 5;87:1580-9
references.pmid: 14306194
references.citation: J Am Chem Soc. 2004 Sep 29;126(38):11810-1
references.pmid: 15382913
references.citation: Chemistry. 2004 Apr 19;10(8):2011-21
references.pmid: 15079841
references.citation: Drugs. 1986;32 Suppl 1:18-26
references.pmid: 2877850
references.citation: Angew Chem Int Ed Engl. 2007;46(38):7266-9
references.pmid: 17579907
references.citation: Science. 2008 Dec 12;322(5908):1661-4
references.pmid: 19074342
references.citation: Org Lett. 2003 Apr 3;5(7):979-82
references.pmid: 12659553
references.citation: Chem Soc Rev. 2012 Mar 7;41(5):1809-25
references.pmid: 22008710
references.citation: Chem Rev. 2007 Mar;107(3):874-922
references.pmid: 17305399
references.citation: Angew Chem Int Ed Engl. 2003 Apr 11;42(14):1566-8
references.pmid: 12698450
references.citation: Analyst. 1967 Apr;92(93):207-38
references.pmid: 4859975
references.citation: J Am Chem Soc. 2006 Jan 11;128(1):56-7
references.pmid: 16390119
references.citation: Am J Gastroenterol. 2002 Dec;97(12):2939-41
references.pmid: 12492172
references.citation: Angew Chem Int Ed Engl. 2011 Feb 7;50(6):1325-7
references.pmid: 21290504
references.citation: Angew Chem Int Ed Engl. 2010 Aug 16;49(35):6174-7
references.pmid: 20652918
references.citation: Org Lett. 2010 Jun 18;12(12):2841-3
references.pmid: 20481477
references.citation: Org Lett. 2013 Apr 19;15(8):1802-5
references.pmid: 23541283
references.citation: Org Lett. 2010 Sep 3;12(17):3902-5
references.pmid: 20681600
references.citation: J Am Chem Soc. 2007 Nov 14;129(45):13784-5
references.pmid: 17958362
references.citation: Org Lett. 2009 Jul 2;11(13):2908-11
references.pmid: 19505125
references.citation: Science. 1995 Jun 30;268(5219):1873-5
references.pmid: 17797528
references.citation: Org Lett. 2013 Mar 1;15(5):1092-5
references.pmid: 23419035
references.citation: Chem Commun (Camb). 2013 Feb 18;49(14):1410-2
references.pmid: 23310929
references.citation: J Phys Chem A. 2005 Sep 15;109(36):8081-7
references.pmid: 16834193