title: Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.
abstract: We report formal [3 + 3] annulations of aromatic azides with aromatic imines and azobenzenes to give acridines and phenazines, respectively. These transformations proceed through a cascade process of Rh(III)-catalyzed amination followed by intramolecular electrophilic aromatic substitution and aromatization. Acridines can be directly prepared from aromatic aldehydes by in situ imine formation using catalytic benzylamine.
authors: Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
authors: Yajing
authors: Y
authors: Lian
authors: Joshua R
authors: JR
authors: Hummel
authors: Robert G
authors: RG
authors: Bergman
authors: Jonathan A
authors: JA
authors: Ellman
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D010619:Phenazines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000166:Acridines; D016566:Organoselenium Compounds; D010619:Phenazines; D012238:Rhodium
references: J Am Chem Soc. 2013 May 15;135(19):7122-5
references: 23642256
references: J Am Chem Soc. 2013 Jan 9;135(1):66-9
references: 23244023
references: Chem Sci. 2012 Jan 1;3(10):3088-3092
references: 23050074
references: Angew Chem Int Ed Engl. 2012 Nov 19;51(47):11819-23
references: 23086779
references: Angew Chem Int Ed Engl. 2012 Sep 3;51(36):8960-9009
references: 22887739
references: Chem Rev. 2010 Feb 10;110(2):624-55
references: 19438203
references: Chemistry. 2013 May 10;19(20):6239-44
references: 23553746
references: Org Lett. 2013 Apr 5;15(7):1638-41
references: 23477353
references: Chem Commun (Camb). 2013 Jun 25;49(50):5654-6
references: 23677037
references: J Am Chem Soc. 2011 Mar 23;133(11):3780-3
references: 21355550
references: Angew Chem Int Ed Engl. 2013 May 27;52(22):5795-8
references: 23606211
references: J Org Chem. 2010 Apr 2;75(7):2289-95
references: 20222700
references: Science. 2012 Oct 26;338(6106):500-3
references: 23112327
references: J Am Chem Soc. 2009 Sep 2;131(34):12050-1
references: 19705909
references: Angew Chem Int Ed Engl. 2008;47(21):4019-22
references: 18418815
references: Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9904-8
references: 22936469
references: J Am Chem Soc. 2011 Mar 2;133(8):2350-3
references: 21275421
references: Org Lett. 2013 Jul 5;15(13):3286-9
references: 23767780
references: Chem Commun (Camb). 2013 Jun 7;49(45):5225-7
references: 23628894
references: Chem Soc Rev. 2011 Sep;40(9):4740-61
references: 21666903
references: Pharmacol Rep. 2011;63(2):305-36
references: 21602588
references: Angew Chem Int Ed Engl. 2013 Jan 7;52(2):629-33
references: 23172703
references: Angew Chem Int Ed Engl. 2012 Sep 10;51(37):9372-6
references: 22907635
references: Appl Microbiol Biotechnol. 2010 May;86(6):1659-70
references: 20352425
references: Chem Commun (Camb). 2009 Sep 14;(34):5061-74
references: 20448953
references: J Am Chem Soc. 2012 Nov 14;134(45):18577-80
references: 23113557
references: J Org Chem. 2009 Aug 21;74(16):6295-8
references: 19572577
references: J Am Chem Soc. 2004 Dec 15;126(49):15999-6006
references: 15584734
references: Org Lett. 2012 Oct 19;14(20):5338-41
references: 23039134
references: J Am Chem Soc. 2010 Aug 4;132(30):10565-9
references: 20662529
references: Angew Chem Int Ed Engl. 2012 Jan 2;51(1):197-200
references: 22086756
references: Chem Soc Rev. 2007 Jul;36(7):1173-93
references: 17576484
references: J Am Chem Soc. 2011 Apr 27;133(16):6449-57
references: 21452842
references: Angew Chem Int Ed Engl. 2012 Apr 16;51(16):3948-52
references: 22396146
references: J Am Chem Soc. 2013 Jun 19;135(24):8802-5
references: 23711098
references: Org Lett. 2013 Apr 19;15(8):1814-7
references: 23560588
references: Angew Chem Int Ed Engl. 2011 Jun 20;50(26):5927-31
references: 21591038
references: J Am Chem Soc. 2013 Apr 10;135(14):5364-7
references: 23548055
references: Org Process Res Dev. 2011 Jul 15;15(4):758-762
references: 21804756
references: Chemistry. 2013 May 10;19(20):6198-202
references: 23589402
references: J Am Chem Soc. 2011 Aug 3;133(30):11430-3
references: 21714533
references: Org Biomol Chem. 2012 Dec 7;10(45):8953-5
references: 23076206
references: J Am Chem Soc. 2010 Jul 21;132(28):9585-7
references: 20578748
references: Angew Chem Int Ed Engl. 2010 Mar 22;49(13):2282-5
references: 20186895
references: Angew Chem Int Ed Engl. 2012 Jul 16;51(29):7318-22
references: 22514051
references: Chem Rev. 2010 Feb 10;110(2):1147-69
references: 20078038
references: J Am Chem Soc. 2010 Oct 13;132(40):14048-51
references: 20858012
references: Angew Chem Int Ed Engl. 2009;48(28):5094-115
references: 19557755
references: Chem Soc Rev. 2012 May 7;41(9):3651-78
references: 22377832
references: J Am Chem Soc. 2008 Sep 17;130(37):12414-9
references: 18714995
references: Chem Commun (Camb). 2011 Nov 28;47(44):12074-6
references: 22006288
references: Chem Commun (Camb). 2012 Jan 7;48(2):308-10
references: 22105760
references: Chemistry. 2013 Jun 3;19(23):7328-33
references: 23616285
references: Science. 2012 Oct 26;338(6106):504-6
references: 23112328
references: Nature. 2008 Jan 24;451(7177):417-24
references: 18216847
references: Org Lett. 2012 Feb 3;14(3):906-9
references: 22263914
references: J Am Chem Soc. 2010 Dec 29;132(51):18326-39
references: 21133376
references: Chemistry. 2011 Nov 4;17(45):12591-5
references: 21972033
references: J Am Chem Soc. 2012 Aug 22;134(33):13565-8
references: 22860697
references: Chemistry. 2010 Oct 4;16(37):11212-22
references: 20740508
references: J Am Chem Soc. 2012 Jun 6;134(22):9110-3
references: 22624801
references: Chem Rev. 2004 Mar;104(3):1663-86
references: 15008629
references: J Am Chem Soc. 2012 Dec 5;134(48):19592-5
references: 23146122