Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates: Formation and characterization of 2H-, 3H- and 4H-azepines
Kyosuke Satake, Ryoichi Okuda, Michiaki Hashimoto, Yasusi Fujiwara, Hideki Okamoto, Masaru Kimura, Shiro Morosawa
Institute for Education and Student Services
Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 3H-azepines. Under similar conditions, methyl 3,6-ditert-butyl-1H-azepine-1-carboxylate gave not only the 3H-azepine but also the isomerized 2H- and 4H-azepines. Application of the reaction to dimethyl and diisopropyl substituted 1H-azepines showed that bulky alkyl group substitution stabilizes the seven-membered azatriene system. The thermal behaviour of the di-tert-butyl substituted azepines is discussed.
Journal of the Chemical Society, Perkin Transactions 1
Azepines
Substitution reactions
Satake, K., Okuda, R., Hashimoto, M., Fujiwara, Y., Okamoto, H., Kimura, M., & Morosawa, S. (1994). Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates: Formation and characterization of 2H-, 3H- and 4H-azepines. Journal of the Chemical Society, Perkin Transactions 1, (13), 1753-1757.
Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates : Formation and characterization of 2H-, 3H- and 4H-azepines. / Satake, Kyosuke; Okuda, Ryoichi; Hashimoto, Michiaki; Fujiwara, Yasusi; Okamoto, Hideki; Kimura, Masaru; Morosawa, Shiro.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 13, 1994, p. 1753-1757.
Satake, K, Okuda, R, Hashimoto, M, Fujiwara, Y, Okamoto, H, Kimura, M & Morosawa, S 1994, 'Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates: Formation and characterization of 2H-, 3H- and 4H-azepines', Journal of the Chemical Society, Perkin Transactions 1, no. 13, pp. 1753-1757.
Satake K, Okuda R, Hashimoto M, Fujiwara Y, Okamoto H, Kimura M et al. Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates: Formation and characterization of 2H-, 3H- and 4H-azepines. Journal of the Chemical Society, Perkin Transactions 1. 1994;(13):1753-1757.
Satake, Kyosuke ; Okuda, Ryoichi ; Hashimoto, Michiaki ; Fujiwara, Yasusi ; Okamoto, Hideki ; Kimura, Masaru ; Morosawa, Shiro. / Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates : Formation and characterization of 2H-, 3H- and 4H-azepines. In: Journal of the Chemical Society, Perkin Transactions 1. 1994 ; No. 13. pp. 1753-1757.
@article{00b58eefabf345488276e636536b61d2,
title = "Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates: Formation and characterization of 2H-, 3H- and 4H-azepines",
abstract = "Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 3H-azepines. Under similar conditions, methyl 3,6-ditert-butyl-1H-azepine-1-carboxylate gave not only the 3H-azepine but also the isomerized 2H- and 4H-azepines. Application of the reaction to dimethyl and diisopropyl substituted 1H-azepines showed that bulky alkyl group substitution stabilizes the seven-membered azatriene system. The thermal behaviour of the di-tert-butyl substituted azepines is discussed.",
author = "Kyosuke Satake and Ryoichi Okuda and Michiaki Hashimoto and Yasusi Fujiwara and Hideki Okamoto and Masaru Kimura and Shiro Morosawa",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
publisher = "Chemical Society",
T1 - Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates
T2 - Formation and characterization of 2H-, 3H- and 4H-azepines
AU - Satake, Kyosuke
AU - Okuda, Ryoichi
AU - Hashimoto, Michiaki
AU - Fujiwara, Yasusi
AU - Okamoto, Hideki
AU - Kimura, Masaru
AU - Morosawa, Shiro
N2 - Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 3H-azepines. Under similar conditions, methyl 3,6-ditert-butyl-1H-azepine-1-carboxylate gave not only the 3H-azepine but also the isomerized 2H- and 4H-azepines. Application of the reaction to dimethyl and diisopropyl substituted 1H-azepines showed that bulky alkyl group substitution stabilizes the seven-membered azatriene system. The thermal behaviour of the di-tert-butyl substituted azepines is discussed.
AB - Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 3H-azepines. Under similar conditions, methyl 3,6-ditert-butyl-1H-azepine-1-carboxylate gave not only the 3H-azepine but also the isomerized 2H- and 4H-azepines. Application of the reaction to dimethyl and diisopropyl substituted 1H-azepines showed that bulky alkyl group substitution stabilizes the seven-membered azatriene system. The thermal behaviour of the di-tert-butyl substituted azepines is discussed.
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1