Abstract
Reaction of N-methyl/isopropylacetonitrilium hexachloroantimonate 1a, b with N-formylbenzotriazole 2 afforded the corresponding iminium salts 4a, b; of which 4a reacts with the oxime derivatives 5a-d to give the corresponding N-oxyiminium salts 6a-d in a good yield (60-92 %). Reaction of N-methylacetonitrilium hexachloroantimonate 1a with norbornene (7) furnished the new ring system 1,4,4a,5,6,7,8,8a-octahydro-5,8-methano-4(2-norbornyl)-naphthridinium hexachloroantimonate 10 in 85 % yield. The Treatment of 10 with DDQ oxidized the two bridged protons and afforded 1,4,5,6,7,8-hexahydro-5,8-methano-4(2-norbornyl)-naphthrdinium hexachloroantimonate 11 in 80% yield.
Keywords: Nitrilium salts, N-formylbenzotriazole, norbornene, Ene product, iminium salts, octahydro-5, 8-methanonaphthridinium salts, salts, 8-methanonaphthridinium, Alkylacetonitrilium Salts, DDQ, Benzotriazole, amide group, IR spectra, oximes, 1H NMR spectra, ClCH2CH2Cl, Crystallization
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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