- Regioselective nucleophilic substitution of 5-bromo-2-methoxytropone
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The reaction of 5-bromo-2-methoxytropone with O- and N-nucleophiles, such as ethanol/potassium carbonate, sodium hydroxide, diethylamine, propylamine, p-chloroaniline/triethylamine, and p-phenylenediamine/triethylamine, gave corresponding 2-O- and 2-N-substituted troponoids. Alkyl diamines reacted with the substrate to produce bis(2-aminotropone)s. In the case of S-nucleophiles as 1-propanethiol, thiophenol, and 4-aminothiophenol with a base, the regioselective substitution at the 5-position occurred. Halogenation reagents, triphenyldibromophosphorane and its dichloro analogue, furnished 2,5-dibromo- and 2,5-dichlorotropones, respectively.
- Sato, Ohki,Nitta, Ai,Yamamoto, Ami
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p. 644 - 650
(2015/02/05)
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- Convenient preparation of heteroazulenes by the reaction of 2-aminotropone with heterocumulenes in the presence of a base
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Reactions of 2-aminotropone with heterocumulenes, N,N'-diphenylcarbodiimide, phenyl isothiocyanate, phenyl isocyanate, and carbon disulfide, in the presence of t-BuOK afforded 1-phenylcycloheptaimidazole-2(1H)-phenylimine, 1-phenylcyclohepataimidazole-2(1H)-thione, 1-phenylcycloheptaimidazol-2(1H)-one along with 2H-cycloheptaoxazol-2-one, and 2H-cycloheptathiazol-2-one along with 2H-cycloheptaoxazole-2-thione in good to moderate yields, respectively.
- Mitsumoto, Yuhki,Nitta, Makoto
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p. 2131 - 2137
(2007/10/03)
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