Reaction of N-Nitro-benzotriazole with Nucleophiles

REFERENCES

• Katritzki , A. R. ; Manju , K. ; Singh , S. K. ; Meher , N. K. Benzotriazole-mediated amino-, alkoxy- and alkylthio-alkylation . Tetrahedron 2005 , 61 , 2555 – 2581 .
   Web of Science ®Google Scholar
• Katritzki , A. R. ; Rogovoy , B. V. Benzotraizole: An ideal synthetic auxiliary . Chem. Eur. J. 2003 , 9 , 4586 – 4593 .
   Web of Science ®Google Scholar
• Katritzki , A. R. ; Denisko , O. V. Designing efficient synthetic routes to polyfunctionality . Pure Appl. Chem. 2000 , 72 , 1597 – 1603 .
   Web of Science ®Google Scholar
• Donghi , M. ; Habermann , J. ; Ley , S. V. Benzotriazoles in solid-phase organic chemistry . Chemtracts 2002 , 15 , 751 – 765 .
   Google Scholar
• Katritzki , A. R. The continuing magic of benzotriazole: An overview of some recent advances in synthetic methodology . J. Heterocycl. Chem. 1999 , 36 , 1501 – 1522 .
   Web of Science ®Google Scholar
• Katritzki , A. R. ; Qi , M. Michael additions of benzotriazole-stabilized carbanions: A review . Coll. Czech. Chem. Commun. 1998 , 63 , 599 – 613 .
   Google Scholar
• Graebe , C. ; Ullmann , F. Ueber eine neue Carbazolsynthese . Liebigs Ann. 1896 , 291 , 16 – 17 .
   Google Scholar
• Ullmann , F. Studien in der Carbazolreihe . Liebigs Ann. 1904 , 332 , 82 – 104 .
   Google Scholar
• Mehta , L. K. ; Parrick , J. ; Payne , F. The elimination of an alkoxy group in the photo-Graebe–Ullmann conversion of 1-(2,5-dialkoxyphenyl)triazolopyridined into carbolines, and the preparation of α-, γ- and δ-carboline quinones . J. Chem. Soc., Perkin Trans. 1 1993 , 1261 – 1267 .
   Google Scholar
• Burgess , E. M. ; Carithers , R. ; McCullagh , L. Photochemical decomposition of 1H- 1,2,3-triazole derivatives . J. Am. Chem. Soc. 1968 , 90 , 1923 – 1924 .
   Web of Science ®Google Scholar
• Katritzky , A. R. ; Rachwal , S. ; Offerman , R. J. ; Najzanek , Z. ; Yagoub , A. K. ; Zhang , Y. Nucleophilic attack at heterocyclic nitrogen: Unusual reactivity of the benzotriazole heterocyclic ring . Chem. Ber. 1990 , 123 , 1545 – 1552 .
   Google Scholar
• Katritzky , A. R. ; Rachwal , S. ; Rachwal , B. Reactions of 1-(α-alkoxyalkyl)- and 1-(α- (aryloxy)alkyl)benzotriazoles with the Grignard reagents: A new and versatile method for the preparation of ethers . J. Org. Chem. 1989 , 54 , 6022 – 6029 .
   Web of Science ®Google Scholar
• Katritzky , A. R. ; Hughes , C. V. ; Rachwal , S. Chemistry of benzotriazoles: Benzotriazol-1-ylmethylammonium salts’ synthesis and reactivity . J. Heterocycl. Chem. 1989 , 26 , 1579 – 1588 .
   Web of Science ®Google Scholar
• Katritzky , A. R. ; Huang , T.-B. ; Denisko , O. V. A novel rearrangement to 1,2,4- triazolo[1,5-a]quinoxalines . J. Org. Chem. 2002 , 67 , 3118 – 2119 .
   Web of Science ®Google Scholar
• Katritzky , A. R. ; Fan , W.-Q. ; Greenhill , J. V. 4-(Benzotriazol-1-yl)-6H- benzo[c]tetrazolo[1,5-e][1,2,5]triazepine, a new heterocyclic ring system formed by a novel benzotriazole ring opening. J. Org. Chem. 1991, 56, 1299–1301.
   Web of Science ®Google Scholar
• Micó , X. A. ; Ziegler , T. ; Subramanian , L. R. A versatile direct approach to ortho- substituted azobenzenes from benzotriazoles . Angew. Chem. 2004 , 116 , 1424 – 1427 ; Angew. Chem., Int. Ed. Engl. 2004, 43, 1400–1403 .
   Google Scholar
• Micó , X. A. ; Richter , M. ; Schwarz , S. ; Strähle , J. ; Ziegler , T. ; Subramanian , L. R. Crystal structure of nonafluoro-{N-[(E)-2-(4-hydroxyphenyl)diazenyl]-phenyl}-1-butanesulfonamide, C16H10F9N3O3S . Z. Kristallogr. NCS 2003 , 218 , 547 – 548 .
   Google Scholar
• Micó , X. A. ; Richter , M. ; Schwarz , S. ; Strähle , J. ; Ziegler , T. ; Subramanian , L. R. Crystal structure of nonafluro-{N-[(E)-2-(2-hydroxyphenyl)diazenyl]-phenyl}-1-butanesulfonamide, C16H10F9N3O3S . Z. Kristallogr. NCS 2003 , 218 , 549 – 550 .
   Google Scholar
• Subramanian , L. R. ; Micó , X. A. ; Ziegler , T. Verfahren zur Herstellung von ortho- und para-substitutierten aromatischen Azoverbindungen sowie anderer Azoverbindungen. Ger. Offen. DE Patent 102004005316, 2005; Chem. Abstr. 143:268286 .
   Google Scholar
• Micó , X. A. ; Vagin , S. I. ; Subramanian , L. R. ; Ziegler , T. ; Hanack , M. New unsymmetrical zinc–phthalocyanine conjugated with one azo-dye moiety: Synthesis via opening the fused triazole ring and spectral properties . Eur. J. Org. Chem. 2005 , 4328 – 4337 .
   Web of Science ®Google Scholar
• Anwar , M. U. ; Tragl , S. ; Ziegler , T. ; Subramanian , L. R. A resourceful access to α-functionalized arylhydrazones . Synlett 2006 , 627 – 629 .
   Web of Science ®Google Scholar
• Micó , X. A. ; Bombarelli , R. G. ; Subramanian , L. R. ; Ziegler , T. Ring opening reactions of benzotriazoles with Wittig reagents . Tetrahedron Lett. 2006 , 47 , 7845 – 7848 .
   Web of Science ®Google Scholar
• Uhde , M. ; Anwar , M. U. ; Ziegler , T. Reaction of N-nonaflyl and N-cyano-benzotriazoles with enamines . Synth. Commun. 2008 , 38 , 881 – 888 .
   Web of Science ®Google Scholar
• Ziegler , T. ; Uhde , M. ; Kirchmann , M. Crystal structure of nonafluorobutane-1-sulfonic acid {2-[4-(4-diethyliminium-but-2-enylidene)-4H-pyridazin-1-yl]-phenyl-imide C22H21F9N4O2S . Z. Kristallogr. NCS 2008 , 223 , 31 – 32 .
   Web of Science ®Google Scholar
• Uhde , M. ; Ziegler , T. Reaction of N-nonaflyl-benzotriazole with silylenolethers . Synthesis 2009 , 1190 – 1194 .
   Google Scholar
• Katritzky , A. R. ; Khelashvili , L. ; Le , K. N. B. ; Mohapatra , P. P. ; Steel , P. J. Synthesis of o-sulfamidotriazobenzenes from 1,1′-sulfonylbis(benzotriazole) . J. Org. Chem. 2007 , 72 , 5805 – 5808 .
   Web of Science ®Google Scholar
• Ketari , R. ; Foucaud , A. Synthesis of 4-bromo-1-nitropyrazoles and 1-nitrobenzotriazoles (N-nitroazoles) . Synthesis 1992 , 844 – 846 .
   Google Scholar
• Cohen-Fernandes , P. ; Habraken , C. L. Nitration of indazoles in the 3 position . J. Org. Chem. 1971 , 36 , 3084 – 3086 .
   Web of Science ®Google Scholar
• Habraken , C. L. ; Erkelens , C. ; Mellema , J. R. ; Cohen-Fernandes , P. 1-Nitrobenzotriazole-2-(nitroimino)diazobenzene isomerization: Formation of triazenes by azo coupling with cyclic amines: Structure determination and dynamic NMR . J. Org. Chem. 1984 , 49 , 2197 – 2200 .
   Web of Science ®Google Scholar
• Colonna , M. ; Poloni , M. Electron-transfer processes: Reaction of electron-rich systems with 1-nitrobenotriazoles . Gazz. Chim. Ital. 1988 , 118 , 673 – 674 .
   Google Scholar
• El-Shihi , T. ; Herrmann , R. A practical synthesis of 2-azidophenylisocyanide . Z. Naturforsch. B 1986 , 41B , 132 – 133 .
   Google Scholar
• Korkin , A. A. ; Leszczynski , J. ; Bartlett , R. J. Theoretical ab initio study of CN2O2 structures: Prediction of nitryl cyanide as a high-energy molecule . J. Phys. Chem. 1996 , 100 , 19840 – 19846 .
   Web of Science ®Google Scholar
• Gauthier , J. ; Duceppe , J. S. Synthesis of novel imidazo[1,2-a][3,1]benzothiazines 4, imidazo[1,2-a]-[1,2,4]benzotriazines 5, and 4H-imidazo[2,3-c]pyrido[2,3-e][1,4]oxazines 6 . J. Heterocycl. Chem. 1984 , 21 , 1081 – 1086 .
   Web of Science ®Google Scholar