以喹啉吡啶类生物碱lupinine为原料合成1,2,3-三唑喹啉吡啶类化合物

Z. Nurmaganbetov, O.A. Hurkenov, S. Fazylov, G.K. Mukusheva, A. Gazaliyev, Z. Muldakhmetov
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引用次数: 1

摘要

采用1,2,3-三唑基取代喹啉菌素主链C-1位置的羟基取代基,对喹啉菌素生物碱羽氨酸进行了改性。在三乙胺存在下,羽衣嘧啶与甲磺酸盐反应顺利,得到羽衣嘧啶甲磺酸盐,再与叠氮化钠在DMFA中反应得到羽衣嘧啶叠氮化钠。1,3-偶极[4+2]-叠氮化物与炔烃的环加成生成了更稳定的1,2,3-三唑化合物。在DMFA培养基中,lupinilazide与2-乙基吡啶和末端含有乙炔基团的醇(丙炔醇、2-甲基-3-in -2-ol或己-5-in -1-ol)的相互作用顺利进行。该反应在CuSO4和抗坏血酸钠水溶液存在的DMFA中进行,并允许以良好的收率合成相应的4-取代(1S,9aR)- 1h -1,2,3-三唑-1-基)甲基八氢- 1h -喹啉菌素。本文给出了合成化合物的1H- NMR和13C - NMR的结构特征研究结果,以及二维COSY (1H-1H)和HMQC (1H-13C)光谱的数据。确定了一维核磁共振谱中1H和13C信号的化学位移、多重度和积分强度的值。在所有合成的新喹诺齐二硝三唑的光谱中,都有一个C10H17N离子(150 ~ 151 cu)的片段峰,对应于喹诺齐啶主链的C-10原子对分子的裂解。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
SYNTHESIS OF 1,2,3-TRIAZOLO-QUINOLIZIDINES BASED ON THE QUINOLIZIDINE ALKALOID LUPININE
The modification of the quinolysin alkaloid lupinine was carried out with the intro-duction of 1,2,3-triazolyl substituents for the hydroxymethylene group in the C-1 position of the quinolysin backbone. The reaction of lupinine with methanesulfochloride in the presence of triethylamine smoothly led to lupinine methanesulfonate, whose further reaction with sodium azide in DMFA led to lupinilazide. 1,3-Dipolar [4+2]-cycloaddition of the resulting azide to alkynes produced more stable 1,2,3-triazole compounds. The interaction of lupinilazide with 2-ethinylpyridine and with alcohols containing a terminal acetylene group (propargyl alcohol, 2-methylbut-3-in -2-ol or hex-5-in -1-ol) proceeded smoothly in the DMFA medium. The reactions were carried out in the presence of an aqueous solution of CuSO4 and sodium ascorbate in DMFA and allowed the corresponding 4-substituted (1S,9aR)-1H-1,2,3-triazol-1-yl to be synthesized with good yields)methyl)octahydro-1H-quinolysins. The results of studying the structural features of synthesized compounds by 1H - and 13C - NMR spectroscopy, as well as data from the two-dimensional COSY (1H-1H) and HMQC (1H-13C) spectra are presented. The values of chemical shifts, multiplicity and integral intensity of 1H and 13C signals in one-dimensional NMR spectra are determined. In the spectra of all synthesized new quinolizi-dinotriazoles, there is a peak of the fragmentary C10H17N ion (150-151 cu), corresponding to the cleavage of the molecule by the C-10 atom of the quinolizidine backbone.
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