フラン誘導体の合成研究 (第10報)

抄録

β-2-(5-Nitro)-furylserine ethyl ester hydrochloride (I), m.p. 175° (decomp.), was prepared by the condensation of 2-(5-nitro)-furfural and glycine ethyl ester, via the intermediate Schiff base. From existing literature and experimental evidences, this substance was assumed to be the DL-compound of erythro-configuration. (I) was respectively condensed with acetyl chloride, benzoyl chloride, p-nitrobenzoyl chloride, p-chlorobenzoyl chloride (b.p₁₈ 115°), 2, 4-dichlorobenzoyl chloride (b.p₃₄ 158°), cinnamoyl chloride (m.p. 35-36°), furoyl chloride (m.p. -2°), 2-(5-nitro)-furoyl chloride (m.p. 34°), furylacryloyl chloride (b.p₆ 106.5°), and 2-(5-nitro)-furylacryloyl chloride (m.p. 99°). The N-acylated erythro-DL-β-[2-(-nitro)-furyl]-serine ethyl esters thereby obtained were as follows: N-acetyl-, m.p. 89°; N-benzoyl-, m.p. 115-117°; N-(p-nitrobenzoyl)-, m.p. 96-97°; N-(p-chlorobenzoyl)-, m.p. 85-86°; N-(2, 4-dichlorobenzoyl)- (or 1-(2, 4-dichlorobenzoylamido)-2-[2-(5-nitro)-furyl]-ethylene), m.p. 229°; N-cinnamoyl-, m.p. 114-115°; N-furoyl-, m.p. 122°; N-[2-(5-nitro)-furoyl]-, m.p. 141°; N-furylacryloyl-, m.p. 188°; N-[2-(5-nitro)-furylacryloyl]-, m.p. 189°.