Copper Powder–Catalyzed C-N Bond Formation of Arylhydrazones of 2-Bromobenzaldehydes Leading to 1-Aryl-1H-indazoles

REFERENCES

• Schmidt , A. ; Beutler , A. ; Snovydovych , B. Recent advances in the chemistry of indazoles . Eur. J. Org. Chem. 2008 , 4073 – 4095 .
   Web of Science ®Google Scholar
• Wolfe , J. P. ; Wagaw , S. ; Marcoux , J.-F. ; Buchwald , S. L. Rational development of practical catalysts for aromatic carbon-nitrogen bond formation . Acc. Chem. Res. 1998 , 31 , 805 – 818 .
   Web of Science ®Google Scholar
• Hartwig , J. F. Transition metal–catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and mechanism . Angew. Chem. Int. Ed. 1998 , 37 , 2046 – 2067 .
   PubMed Web of Science ®Google Scholar
• Yang , B. H. ; Buchwald , S. L. Palladium-catalyzed amination of aryl halides and sulfonates . J. Organomet. Chem. 1999 , 576 , 125 – 146 .
   Web of Science ®Google Scholar
• Song , J. J. ; Yee , N. K. A novel synthesis of 2-aryl-2H-indazoles via a palladium-catalyzed intramolecular amination reaction . Org. Lett. 2000 , 2 , 519 – 521 .
   PubMed Web of Science ®Google Scholar
• Wagaw , S. ; Yang , B. H. ; Buchwald , S. L. A palladium-catalyzed strategy for the preparation of indoles: A novel entry into the Fischer indole synthesis . J. Am. Chem. Soc. 1998 , 120 , 6621 – 6622 .
   Web of Science ®Google Scholar
• Haddad , N. ; Baron , J. Novel application of the palladium-catalyzed N-arylation of hydrazones to a versatile new synthesis of pyrazoles . Tetrahedron Lett. 2002 , 43 , 2171 – 2173 .
   Web of Science ®Google Scholar
• Haddad , N. ; Salvagno , A. ; Busacca , C. Application of the palladium-catalyzed N-arylation of hydrazones to deactivated heteroaryl halides in the synthesis of pyrazoles . Tetrahedron Lett. 2004 , 45 , 5935 – 5937 .
   Web of Science ®Google Scholar
• Cho , C. S. ; Patel , D. B. Palladium-catalyzed C-N bond formation: Synthesis of 1-aryl-1H-pyrazoles from β-bromovinyl aldehydes and arylhydrazines . Tetrahedron 2006 , 62 , 6388 – 6391 .
   Web of Science ®Google Scholar
• Song , J. J. ; Yee , N. K. Synthesis of 1-aryl-1H-indazoles via the palladium-catalyzed cyclization of N-aryl-N′-(o-bromobenzyl)hydrazines and [N-aryl-N′-(o-bromobenzyl)-hydrazinato-N′]triphenylphosphonium bromides . Tetrahedron Lett. 2001 , 42 , 2937 – 2940 .
   Web of Science ®Google Scholar
• Lebedev , A. Y. ; Khartulyari , A. S. ; Voskoboynikov , A. Z. Synthesis of 1-aryl-1H-indazoles via palladium-catalyzed intramolecular amination of aryl halides . J. Org. Chem. 2005 , 70 , 596 – 602 .
   PubMed Web of Science ®Google Scholar
• Inamoto , K. ; Katsuno , M. ; Yoshino , T. ; Suzuki , I. ; Hiroya , K. ; Sakamoto , T. Efficient synthesis of 3-substituted indazoles using Pd-catalyzed intramolecular amination reaction of N-tosylhydrazones . Chem. Lett. 2004 , 33 , 1026 – 1027 .
   Web of Science ®Google Scholar
• Inamoto , K. ; Katsuno , M. ; Yoshino , T. ; Arai , Y. ; Hiroya , K. ; Sakamoto , T. Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: Application to the synthesis of nigellicine . Tetrahedron 2007 , 63 , 2695 – 2711 .
   Web of Science ®Google Scholar
• Dong , C. ; Xie , L. ; Mou , X. ; Zhong , Y. ; Su , W. Facile synthesis of 1,3,4-benzotriazepines and 1-arylamide-1H-indazoles via palladium-catalyzed cyclization of aryl isocyanates and aryl hydrazones under microwave irradiation . Org. Biomol. Chem. 2010 , 8 , 4827 – 4830 .
   PubMed Web of Science ®Google Scholar
• Suryakiran , N. ; Prabhakar , P. ; Venkateswarlu , Y. Synthesis of 3-amino-substituted N-alkylindazoles via palladium(II)-catalyzed intramolecular N-arylation of tosylhydrazines . Chem. Lett. 2007 , 36 , 1370 – 1371 .
   Web of Science ®Google Scholar
• Viña , D. ; del Olmo , E. ; López-Pérez , J. L. ; Feliciano , A. S. Regioselective synthesis of 1-alkyl- or 1-aryl-1H-indazoles via copper-catalyzed cyclization of 2-haloarylcarbonylic compounds. Org. Lett. 2007, 9, 525–528.
   PubMed Web of Science ®Google Scholar
• Liu , R. ; Zhu , Y. ; Qin , L. ; Ji , S. Efficient synthesis of 1-aryl-1H-indazole derivatives via copper(I)-catalyzed intramolecular amination reaction . Synth. Commun. 2008 , 38 , 249 – 254 .
   Web of Science ®Google Scholar
• Kylmälä , T. ; Udd , S. ; Tois , J. ; Franzén , R. (Z)-Selective synthesis of o-bromoacetophenone N-tosylhydrazones and formation of 3-methylindazoles in aqueous ethanol . Tetrahedron Lett. 2010 , 51 , 3613 – 3615 .
   Google Scholar
• Pabba , C. ; Wang , H. ; Mulligan , S. R. ; Chen , Z. ; Stark , T. M. ; Gregg , B. T. Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones . Tetrahedron Lett. 2005 , 46 , 7553 – 7557 .
   Web of Science ®Google Scholar
• Cho , C. S. ; Lim , D. K. ; Heo , N. H. ; Kim , T.-J. ; Shim , S. C. Facile palladium-catalysed synthesis of 1aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines . Chem. Commun. 2004 , 104 – 105 .
   PubMed Web of Science ®Google Scholar
• Cho , C. S. ; Tran , N. T. Nickel(0) powder catalysis in Suzuki–Miyaura cross-coupling reaction . Catal. Commun. 2009 , 11 , 191 – 195 .
   Web of Science ®Google Scholar