title: Facile one-pot assembly of imidazotriazolobenzodiazepines via indium(III)-catalyzed multicomponent reactions.
abstract: An operationally simple, one-pot multicomponent reaction has been developed for the assembly of 9H-benzo[f]imidazo[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepines adorned with three diversification points via an atom-economical transformation incorporating α-diketones, o-azidobenzaldehydes, propargylic amines, and ammonium acetate. This process involves tandem InCl3-catalyzed cyclocondensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions; optimization data, substrate scope, and mechanistic insights are discussed.
authors: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA.
authors: Huy H
authors: HH
authors: Nguyen
authors: Teresa A
authors: TA
authors: Palazzo
authors: Mark J
authors: MJ
authors: Kurth
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D000588:Amines; D001386:Azides; D006576:Heterocyclic Compounds, 4 or More Rings; D014230:Triazoles; D007204:Indium
references: Org Lett. 2011 Mar 4;13(5):852-5
references: 21275426
references: J Med Chem. 2013 Feb 28;56(4):1656-69
references: 23360431
references: Beilstein J Org Chem. 2013 Oct 14;9:2097-102
references: 24204421
references: J Am Chem Soc. 2011 Apr 6;133(13):4702-5
references: 21401042
references: Angew Chem Int Ed Engl. 2006 Feb 13;45(8):1282-4
references: 16425308
references: Org Lett. 2012 Aug 3;14(15):3870-3
references: 22823414
references: Org Lett. 2008 Apr 17;10(8):1617-9
references: 18348569
references: Bioorg Med Chem Lett. 2012 Feb 1;22(3):1317-21
references: 22225635
references: J Med Chem. 2006 Mar 23;49(6):2037-48
references: 16539392
references: Eur J Med Chem. 2004 Sep;39(9):805-14
references: 15337293
references: Angew Chem Int Ed Engl. 2011 Aug 29;50(36):8316-9
references: 21780265
references: Org Lett. 2012 Jul 20;14(14):3732-5
references: 22746550
references: J Med Chem. 2012 Mar 8;55(5):2144-53
references: 22332894
references: Eur J Med Chem. 2013 May;63:897-906
references: 23631874
references: Eur J Med Chem. 2008 Aug;43(8):1721-9
references: 17845827
references: Org Lett. 2012 Apr 6;14(7):1804-7
references: 22440058
references: J Med Chem. 2004 Dec 2;47(25):6311-25
references: 15566301
references: J Appl Toxicol. 2001 Dec;21 Suppl 1:S115-9
references: 11920931
references: ACS Comb Sci. 2012 Feb 13;14(2):135-43
references: 22273436
references: Bioorg Med Chem Lett. 2009 Sep 1;19(17):5241-5
references: 19648009
references: Org Lett. 2013 Apr 19;15(8):1874-7
references: 23544989