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Short Paper | Regular issue | Vol 94, No. 11, 2017, pp.2087-2094
Published online, 15th September, 2017
DOI: 10.3987/COM-17-13795
■ Synthesis of 8,9-Dihydropyrimido[4,5-e][1,4]oxazepin-7(5H)-ones by the Reaction of 1-(4-Chloropyrimidin-5-yl)alkan-1-ols with N-Alkylglycines

Kazuhiro Kobayashi,* Takashi Nogi, Yuka Tsunomori, Hidetaka Hiyoshi, and Kazuto Umezu

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A facile method for the construction of a new ring system, 8,9-dihydropyrimido[4,5-e][1,4]oxazepin-7(5H)-one, is described. The key feature of the synthetic route includes substitution of one of the two chloro groups of 1-(4,6-dichloropyrimidin-5-yl)alkan-1-ol derivatives, which can easily be derived from the reaction between 5-lithiated compound of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP) and aldehydes, with N-alkylglycines in the presence of triethylamine, followed by lactonization of the resulting hydroxy acids catalyzed by in situ generated triethylamine hydrochloride.