165461-04-1Relevant articles and documents
Zirconocene-mediated synthesis of 3,4-disubstituted piperidines and reduced isoquinolines
Kemp, Mark I.,Whitby, Richard J.,Coote, Steven J.
, p. 557 - 568 (2007/10/03)
Intramolecular cocyclisation of 4-azaocta-1,7-dienes, -1-en-7-ynes, -7- en-1-ynes and -1,7-diynes using 'zirconocene' equivalents affords 3-aza-8- zirconabicyclo[4.3.0]nonanes, -6-enes, -9-enes or -6,9-dienes. Protonolysis, iodinolysis, or carbonylation of these complexes affords 3,4-disubstitued piperidines. Exocyclic 1,3-dienes formed from the coupling/protonolysis of 4- azaocta-1,7-diynes react with activated dienophiles to yield reduced isoquinolines.
The cobalt-mediated [2+2+2] cycloaddition of α,ω-diynes to the 2,3-double bond of indole
Boese,Van Sickle,Vollhardt
, p. 1374 - 1382 (2007/10/02)
The reaction of acetyl or phenylsulfonylindole with α,ω-diynes and CpCo(C2H4)2 yields CpCo-complexed dihydrocarbazoles. 1-Trimethylsilyl-1,6-heptadiyne gives an adduct in which the silyl moiety is distal to the phenylsulfonamide. 1-Trimethylsilyl-1,7-octadiyne results in an unusual diene complex resulting from C-H activation at C-2 of the indole. The behavior of a number of terminally substituted 4-aza, 1,7-octadiynes to the reaction is investigated. The oxidation of one dihydrocarbazole complex with triphenylcarbenium hexafluorophosphate or with Fe(NO3)3 furnishes an η5-cyclohexadienyl cobalt complex and its subsequent conversion into substituted diene complexes or to the demetallated carbazole is discussed.
