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Hideki Okamoto
Divisi Kimia dan Biokimia Program Pascasarjana Ilmu Pengetahuan Alam dan Teknologi Universitas Okayama 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Jepang
Environmental Science

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Synthesis of 2-Methoxy-3H-Azepine Derived Compounds Through the Thermal Reaction between Alkylnitrobenzene and Tributylphosphine Siti Mariyah Ulfa; Hideki Okamoto; Kyosuke Satake
Natural B, Journal of Health and Environmental Sciences Vol 3, No 1 (2015)
Publisher : Natural B, Journal of Health and Environmental Sciences

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (531.661 KB) | DOI: 10.21776/ub.natural-b.2015.003.01.3

Abstract

Although photolysis of phenyazide has been widely reported to give 3H-azepine, the thermal deoxygenation reaction of alkylnitrobenzene derived similar products hitherto unexplored. Novel synthesis of 2-methoxy-3H-azepine derivatives was carried out using alkylnitrobenzene with tributylphosphine (Bu3P) reacted at 150°C for 24 hours in the presence of methanol. Reaction of m-nitrobenzene with the above methods gave two isomers of 3H-azepine, namely, 2-methoxy-6-methyl-3H-azepine and 2-methoxy-4-methyl-3H-azepine in 61%. Reaction of 2,3-dimethylnitrobenzene with Bu3P afforded the three isomers, that is, 2-methoxy-6,7-dimethyl-3H-azepine; 2-methoxy-3,4-dimethyl-3H-azepine and 7-methoxy-5,6-dimethyl-4H-azepine. Reaction of 3,5-dimethylnitrobenzene gave the sole product of 2-methoxy-4,6-dimethyl-3H-azepine in 42%. In contrast, reaction of 2,6-dimethylnitrobenzene didn’t give any product because the steric effect of methyl groups attached on C2 and C6. Structure elucidation of all novel products have confirmed by HETCOR. 
Co-Authors Kyosuke Satake Siti Mariyah Ulfa