Seiji Miyano

Synthesis of 2-Phenyl-2,3,4,5-tetrshydro-1-benzoxepin-5-ones

A series of 2-phenyl-2,3,4,5-tetrahydro-1-benzoxepin-5-ones were synthesized by 2 steps from flavones through 3,4-benzo-5-oxo-2-oxabicyclo[4.1.0]heptanes.

Reactions of enamino-ketones. Part II. Synthesis of 4H-1,4-benzothiazines

A new synthesis of 4H-1,4-benzothiazines, consisting of the condensation of o-aminobenzenethiol with cyclohexane-1,3-diones, acetylacetone, benzoylacetone, or ethyl acetoacetate in dimethyl sulphoxide, is described. An oxidative cyclisation mechanism, involving an intramolecular nucleophilic attack in an intermediate enaminoketone, is suggested.

Synthesis of 2,3-dihydro-1H-phenothiazin-4(10H)-ones

2,3-Dihydro-1H-phenothiazin-4(10H)-ones (4)–(7) were prepared by condensation of o-aminobenzenethiol (1) with cyclohexane-1,3-diones (2) in Me2SO.

Synthesis of 5,9,9-trisubstituted 1-azabicyclo[3.3.1]nonanes and their conformational analyses

A new route for the preparation of 1-azabicyclo[3.3.1]nonane (1) and related compounds, consisting of the reactions similar to the skeletal rearrangement of 2,3,5,6,7,7a-hexahydro-7a-trichloromethylpyrrolizine (2) into 5,9,9-trichloro-1-azabicyclo[3.3.1]nonane (3), is described. The conformational analysis and some chemical properties of the products are also mentioned.

Studies on pyrrolizidines and related compounds. Part 9. Rearrangement of 7a-trichloromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine and related compounds: an alternative route to 5-substituted 1-azabicyclo[3.3.1]nonanes

Rearrangement of 7a-trichloromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine and related compounds provides a new synthesis of 1-azabicyclo [3.3.1] nonanes.

Studies on pyrrolizidines and related compounds. Part 8. A new route to perhydroazocines and related compounds using 1,2,3,5,6,7-hexahydropyrrolizinylium perchlorate

A new method for the synthesis of 5-substituted perhydroazocines and related compounds is described. The method consists of the C(7a)–N(4) bond cleavage of quaternary ammonium salts of 7a-substituted hexahydropyrrolizines which are easily prepared from 1,2,3,5,6,7-hexahydropyrrolizinylium perchlorate.