121198-57-0Relevant articles and documents
A New and Safe Approach to (N-Vinylimino)phosphoranes
Katritzky, Alan R.,Mazurkiewicz, Roman,Stevens, Christian V.,Gordeev, Mikhail F.
, p. 2740 - 2742 (2007/10/02)
1-benzotriazoles, obtained by Staudinger phosphenimide-forming reaction of (azidoalkyl)benzotriazoles, possessing a proton in a β-position to nitrogen reacted with sodium hydride in THF to afford (N-vinylimino)phosphoranes in high yields.The latter were trapped with chalcone to give the corresponding 2,4-diphenylpyridines.
On the Reaction of N-Vinyliminophosphoranes. Part 7. A Short New 1-Aza-azulene Synthesis
Nitta, Makoto,Iino, Yukio,Hara, Eijiro,Kobayashi, Tomoshige
, p. 51 - 56 (2007/10/02)
Thermal reaction of triphenyl(vinylimino)phosphorane derivatives with several tropones have been studied to provide a short new route to the 1-aza-azulene ring system. (1-Phenylvinylimino)-, vinylimino-, and a mixture of (1-butylvinylimino)- and (1-methylpent-1-enylimino)-triphenylphosphorane were treated with tropone and alkylated tropones in an enamine alkylation process, and the subsequent aza-Wittig reaction resulted in the formation of 1,8-dihydrocycloheptapyrroles.The pyrrole derivatives were easily dehydrogenated by nickel peroxide or manganese dioxide to give 1-aza-azulene derivatives.In a similar fashion, the iminophosphoranes were treated with 2-bromotropone or with 2-chlorotropone in the presence of triethylamine to give 1-aza-azulenes in a single step.The 1-aza-azulenes, which were halogenated on the seven-membered ring, were also prepared conveniently by the reaction of triphenyl(1-phenylvinylimino)phosphorane with 2,7-dibromo-, 2,4,7-tribromo-, and 2,3,5,7-tetrachlorotropone, albeit in modest yields.
Preparation of Novel N-Vinyl-, N-(1-Butylvinyl)-, and N-(1-methyl-1-pentenyl)iminotriphenylphosphoranes and Their Reactions with α,β-Unsaturated Ketones
Iino, Yukio,Nitta, Makoto
, p. 2235 - 2237 (2007/10/02)
The novel N-vinyl- (2a) and a mixture of N-(1-butylvinyl)- (2b) and N-(1-methyl-1-pentenyl)iminotriphenylphosphoranes (2c) were prepared by the reaction of azidoethylene and 2-azido-1-hexene with triphenylphosphine, respectively.The thermal reaction of 2a, 2b, and 2c with α,β-unsaturated ketones undergoes an enamine-type alkylation and the subsequent aza-Wittig reaction to give pyridine derivative in modest yields.
