39183-99-8Relevant academic research and scientific papers
Effective methods for introducing some aryl and heteroaryl substituent onto 1-azaazulene nuclei
Abe, Noritaka,Tanaka, Megumi,Maeda, Takeshi,Fujii, Hiroyuki,Kakehi, Akikazu
, p. 229 - 240 (2007/10/03)
Introduction of aryl and heteroaryl groups onto 1-azaazulene ring was achieved by addition-elimination reaction and Suzuki coupling. Reaction of 2-chloro-1-azaazulenes with 2-aryllithium and 2-heteroaryllithium followed by dehydrogenation with o-chloranil
Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone O-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization and Oxidation
Chiba, Shunsuke,Kitamura, Mitsuru,Saku, Osamu,Narasaka, Koichi
, p. 785 - 796 (2007/10/03)
Various 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by treatment with a catalytic amount of Pd(dba) 2-t-Bu3P (dba = dibenzylideneacetone) and triethylamine in the presence of MS 4A via alkylideneaminopalladium(II) intermediates generated by oxidative addition of the oximes to a Pd(0) complex.
Palladium-catalyzed synthesis of 1-azaazulenes from cycloheptatrienylmethyl ketone O-pentafluorobenzoyl oximes
Kitamura, Mitsuru,Chiba, Shunsuke,Saku, Osamu,Narasaka, Koichi
, p. 606 - 607 (2007/10/03)
Substituted 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by the intra-molecular Heck-type amination catalyzed by Pd(dba)2-(t-Bu)3P.
Novel preparation and reaction of N-benzenesulfonyl- and N-methanesulfonyltroponimines. New entry to 1-azaazulene derivatives
Takayasu, Tohru,Katayama, Hiroshi,Nitta, Makoto
, p. 567 - 574 (2007/10/03)
N-Benzenesulfonyl- and N-methanesulfonyltroponimines were prepared through the reaction of tropone oxime with benzenesulfinyl- and methanesulfinyl chloride. The troponimines reacted with enamines to give formal [8 + 2] cycloadducts, which subsequently und
Synthesis and reactivity of N-diphenylphosphinoyltroponimine: Synthetic entry into 1-azaazulene derivatives
Takayasu, Tohru,Ito, Koji,Nitta, Makoto
, p. 2667 - 2677 (2007/10/03)
A novel N-diphenylphosphinoyltroponimine (5), which is highly polarized and has a low lying LUMO, was prepared. The attempted reaction of 5 with enolate ions and enamines derived from cyclic ketones gave 1-azaazulene derivatives, albeit in low yields.
A New Route To 1-Azaazulene Ring System By The Reaction Of 1-(Diphenylphosphinyl)azaallyl Anions With Tropone Derivatives
Ito, Koji,Nitta, Makoto
, p. 2247 - 2254 (2007/10/02)
The reaction of 1-(diphenylphosphinyl)azaallyl anions derived from the corresponding imines, with tropones underwent enamine-type alkylation and mainly followed by aza-Wittig reaction to give 1-azaazulene derivatives, in addition to a trace amount of 4H-4
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.
ON THE REACTION OF N-VINYLIMINOPHOSPHORANES. 9. THE SYNTHESIS AND REACTION OF N-(1,3,5-CYCLOHEPTATRIENYL)IMINOPHOSPHORANES TO PROVIDE A NOVEL ROUTE TO 1-AZAAZULENES
Iino, Yukio,Hara, Eijiro,Nitta, Makoto
, p. 1913 - 1916 (2007/10/02)
The first syntheses of N-(2,4,6-cycloheptatrienyl)iminophosphoranes (3a, b) and their thermal conversion to N-(1,3,5-cycloheptatrienyl)iminophosphoranes (5a, b) have been studied.The kinetic study of the 1,5-hydrogen migration of 3a, b to N-(1,3,6-cyclohe
ON THE REACTION OF N-VINYLIMINOPHOSPHORANES. A NOVEL ROUTE TO 1-AZAAZULENE RING SYSTEM UTILIZING AZA-WITTIG REACTION
Nitta, Makoto,Kobayashi, Tomoshige
, p. 463 - 466 (2007/10/02)
N-(1-Phenyl)vinyliminotriphenylphosphorane, conveniently prepared from α-azidostyrene and triphenylphosphine, readily undergoes an annulation reaction with tropone derivatives to result in the formation of 1-azaazulene ring system.
