Metal-Free–Catalyzed Oxidative Trimerization of Indoles Using NaNO₂ to Construct Quaternary Carbon Centers: Synthesis of 2-(1H-Indol-3-yl)-2,3′-biindolin-3-ones

REFERENCES

• (a) Ding , Y.-S. ; Gruschow , S. ; Greshock , T. J. ; Finefield , J. M. ; Sherman , D. H. ; Williams , R. M. Detection of VM55599 and preparaherquamide from Aspergillus japonicus and Penicillium fellutanum: Biosynthetic implications . J. Nat. Prod. 2008 , 71 , 1574 – 1578 ; (b) Sun , W. S. ; Hong , L. ; Wang , R. Facile creation of 2-substituted indolin-3-ones by using primary–secondary diamine catalysts . Chem. Eur. J. 2011 , 17 , 6030 – 6037 .
   PubMed Web of Science ®Google Scholar
• (a) Gazit , A. ; Osherov , N. ; Posner , I. ; Yaish , P. ; Poradosu , E. ; Gilon , C. ; Levitzki , A. Tyrphostins, 2: Heterocyclic and alpha-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases . J. Med. Chem. 1991 , 34 , 1896 – 1907 ; (b) Dilber , S. ; Saban , M. ; Jelaca , J. ; Gelineo , A. ; Arsenijevic , L. ; Bogavac , M. Investigation of antimicrobial activity of some isatine derivatives . Pharmazie 1989 , 44 , 649 – 650 ; (c) Wetzel , A. ; Gagosz , F. Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks . Angew. Chem. Int. Ed. 2011 , 50 , 7354 – 7358 ; (d) Kumar , C. V. S. ; Puranik , V. G. ; Ramana , C. V. InCl3-mediated addition of indole to isatogens: an expeditious synthesis of 13-deoxy-isatisineA . Chem. Eur. J. 2012 , 18 , 9601 – 9611 .
   PubMed Web of Science ®Google Scholar
• (a) Bell , R. ; Carmeli , S. ; Sar , N. Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish ostracion cubicus . J. Nat. Prod. 1994 , 57 , 1587 – 1590 ; (b) Stull , T. L. ; Hyun , L. ; Sharetzsky , C. ; Wooten , J. ; McCauley , J. P. ; Smith Ш , A. B. Production and oxidation of indole by Haemophilus influenzae . J. Biol. Chem. 1995 , 270 , 5 – 8 .
   PubMed Web of Science ®Google Scholar
• (a) Liu , J. F. ; Jiang , Z. Y. ; Wang , R. R. ; Zheng , Y. T. ; Chen , J. J. ; Zhang , X. M. ; Ma , Y. B. A novel alkaloid from leaves of Isatis indigotica Fort . Org. Lett. 2007 , 9 , 4127 – 4129 ; (b) Lee , J. ; Panek , J. S. Total synthesis of (+)-isatisine A . Org. Lett. 2011 , 13 , 502 – 505 ; (c) Zheng , H. Z. ; Dong , Z. H. ; Yu , Q. Modern Study of Traditional Chinese Medicine; Xueyaun Press: Beijing, China, 1997; vol. 1, pp. 328–334.
   PubMed Web of Science ®Google Scholar
• (a) Zhang , X. ; Mu , T. ; Zhan , F. X. ; Ma , L. J. ; Liang , G. X. Total synthesis of (-)-isatisine A. Angew. Chem. Int. Ed. 2011, 50, 6164–6166; (b) Rueping , M. ; Raja , S. ; Núñez , A. Asymmetric Brønsted acid–catalyzed Friedel–Crafts reactions of indoles with cyclic imines: Efficient generation of nitrogen-substituted quaternary carbon centers. Adv. Synth. Catal. 2011, 353, 563–568; (c) Wu , W. ; Xiao , M. X. ; Wang , J. B. ; Li , Y. ; Xie , Z. X. Biomimetic total synthesis of (–)-isatisine A. Org. Lett. 2012, 14, 1624–1627; (d) Karadeolian , A. ; Kerr , M. A. Total synthesis of (+)-isatisine A. J. Org. Chem. 2010, 75, 6830–6841; (e) Karadeolian , A. ; Kerr , M. A. Total synthesis of (+)-isatisine A. Angew. Chem. Int. Ed. 2010, 49, 1133–1135.
   PubMed Web of Science ®Google Scholar
• (a) Ganachaud , C. ; Garfagnoli , V. ; Tron , T. ; Iacazio , G. Trimerisation of indole through laccase catalysis . Tetrahedron Lett. 2008 , 49 , 2476 – 2478 ; (b) Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. O. ; Khorshidi , A. Ruthenium-catalyzed efficient routes to oxindole derivatives . Can. J. Chem. 2009 , 87 , 1213 – 1217 ; (c) Rad-Moghadam , K. ; Shari-Kiasaraie , M. ; Taheri- Amlashi , H. Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids . Tetrahedron 2010 , 66 , 2316 – 2321 .
   Web of Science ®Google Scholar
• Qin , W. B. ; Chang , Q. ; Bao , Y. H. ; Wang , N. ; Chen , Z. W. ; Liu , L. X. Metal-free-catalyzed oxidative trimerization of indoles by using TEMPO in air: A biomimetic approach to 2-(1H-indol-3-yl)-2,3′-biindolin-3-ones . Org. Biomol. Chem. 2012 , 10 , 8814 – 8821 .
   PubMed Web of Science ®Google Scholar
• For selected examples using NaNO2 as catalyst, see (a) Su , B. ; Deng , M. ; Wang , Q. M. Bioinspired construction of a spirocyclohexadienone moiety via sodium nitrite–catalyzed aerobic intramolecular oxidative phenol coupling . Org. Lett. 2013 , 15 , 1606 – 1609 ; (b) Su , S. ; Li , L. ; Hu , Y. N. ; Liu , Y. X. ; Wang , Q. M. A novel sodium nitrite–catalyzed oxidative coupling for constructing polymethoxyphenanthrene rings . Adv. Synth. Catal. 2012 , 354 , 383 – 387 ; (c) Stavber , G. ; Iskra , J. ; Zupan , M. ; Stavber , S. Aerobic oxidative iodination of organic compounds with iodide catalyzed by sodium nitrite . Adv. Synth. Catal. 2008 , 350 , 2921 – 2929 ; (d) Liang , X. M. ; Fu , D. M. ; Liu , R. H. ; Zhang , Q. ; Zhang , T. Y. ; Hu , X. Q. Highly efficient NaNO2-catalyzed destruction of trichlorophenol using molecular oxygen . Angew. Chem. Int. Ed. 2005 , 44 , 5520 – 5523 .
   PubMed Web of Science ®Google Scholar
• Qu , H. E. ; Qin , W. B. ; Chang , Q. ; Hu , Q. S. ; Liu , L. X. Iron(Ш) trichloride–catalyzed one-pot three-component coupling of indoles and sodium nitrite: A convenient synthesis of 2,3′-bi(3H-indol)-3-one oximes . Curr. Org. Chem. 2013 , 17 , 756 – 762 .
   Web of Science ®Google Scholar
• Astolfi , P. ; Panagiotaki , M. ; Rizzoli , C. ; Greci , L. Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent . Org. Biomol. Chem. 2006 , 4 , 3282 – 3290 .
   PubMed Web of Science ®Google Scholar