Ugi四组分一锅法高效合成结构独特的活性生物碱化合物

doi:10.3866/PKU.DXHX201910060

Abstract

Abstract:

Using α-amino acids, aldehydes, isocyanides and alcohols as the starting materials, four components react in one pot at room temperature to obtain naturally unique bioactive alkaloids, 1, 1'-iminodicarboxylic acid derivatives. The reaction process is monitored by thin layer chromatography and liquid chromatography-mass spectrometry, and the products are purified by silica gel column chromatography. The structures are determined by mass spectrometry and nuclear magnetic resonance spectroscopy. The reaction is an innovative development of Ugi reaction, which has the characteristics of simple reaction operation, high yield, good stereoselectivity and high atomic economy. It has been widely used in the design and synthesis of new drugs, combinatorial chemistry and natural product synthesis.

Key words: Ugi reaction, Multi-component reaction, 1, 1'-iminodicarboxylic acid derivatives, Alkaloid, One-pot reaction

Houjin Li, Yang Xu, Yunzhu Zhong, Xiaoyan Zhang, Fang Zhu, Liuping Chen. Synthesis of Unique Bioactive Alkaloids by Ugi Four-Component One-Pot Reaction[J].University Chemistry, 2020, 35(4): 178-186.

Figures/Tables 11

References 11

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产物编号	反应原料			产物分子式	产物分子量(m/z)	实际测得的分子量(m/z)
产物编号	氨基酸	醛	异腈	产物分子式	产物分子量(m/z)	实际测得的分子量(m/z)
1	L-色氨酸	异丁醛	叔丁基异腈	C₂₁H₃₁N₃O₃	373	374 [M + H]⁺, 396 [M + Na]⁺
2			异氰基乙酸乙酯	C₂₁H₂₉N₃O₅	403	404 [M + H]⁺, 426 [M + Na]⁺
3			苄基异腈	C₂₄H₂₉N₃O₃	407	408 [M + H]⁺, 430 [M + Na]⁺
4			环己基异腈	C₂₃H₃₃N₃O₃	399	400 [M + H]⁺, 422 [M + Na]⁺
5		苯甲醛	叔丁基异腈	C₂₄H₂₉N₃O₃	407	408 [M + H]⁺, 430 [M + Na]⁺
6			异氰基乙酸乙酯	C₂₄H₂₇N₃O₅	437	438 [M + H]⁺
7			苄基异腈	C₂₇H₂₇N₃O₃	441	442 [M + H]⁺
8			环己基异腈	C₂₆H₃₁N₃O₃	433	434 [M + H]⁺
9		对羟基苯甲醛	叔丁基异腈	C₂₄H₂₉N₃O₄	423	424 [M + H]⁺
10		4-氟-3-硝基苯甲醛	叔丁基异腈	C₂₄H₂₇FN₄O₅	470	469 [M ? H]^?
11	L-酪氨酸	异丁醛	叔丁基异腈	C₁₉H₃₀N₂O₄	350	351 [M + H]⁺, 373 [M + Na]⁺
12	L-酪氨酸	苯甲醛		C₂₂H₂₈N₂O₄	384	385 [M + H]⁺, 407 [M + Na]⁺
13	L-苏氨酸	异丁醛		C₁₄H₂₈N₂O₄	288	289 [M + H]⁺, 311 [M + Na]⁺
14	L-苏氨酸	苯甲醛		C₁₇H₂₆N₂O₄	322	323 [M + H]⁺, 345 [M + Na]⁺
15	L-丝氨酸	异丁醛		C₁₃H₂₆N₂O₄	274	275 [M + H]⁺
16	L-丝氨酸	苯甲醛		C₁₆H₂₄N₂O₄	308	347 [M + K]⁺
17	L-天冬酰胺	异丁醛		C₁₄H₂₇N₃O₄	301	302 [M + H]⁺
18	L-天冬酰胺	苯甲醛		C₁₇H₂₅N₃O₄	335	336 [M + H]⁺, 358 [M + Na]⁺
19	L-谷氨酰胺	异丁醛		C₁₅H₂₉N₃O₄	315	316 [M + H]⁺
20	L-谷氨酰胺	苯甲醛		C₁₈H₂₇N₃O₄	349	350 [M + H]⁺, 372 [M + Na]⁺
21	L-蛋氨酸	异丁醛		C₁₅H₃₀N₂O₃S	318	319 [M + H]⁺
22	L-蛋氨酸	苯甲醛		C₁₈H₂₈N₂O₃S	352	353 [M + H]⁺

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Synthesis of Unique Bioactive Alkaloids by Ugi Four-Component One-Pot Reaction

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