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Multi-component cascade reaction of 3-formylchromones: highly selective synthesis of 4,5-dihydro-[4,5′-bipyrimidin]-6(1H)-one derivatives
Chemical Communications ( IF 4.3 ) Pub Date : 2021-07-01 , DOI: 10.1039/d1cc02437j Li Chen 1 , Rong Huang 1 , Xing-Han Yun 1 , Tian-Hui Hao 1 , Sheng-Jiao Yan 1
Chemical Communications ( IF 4.3 ) Pub Date : 2021-07-01 , DOI: 10.1039/d1cc02437j Li Chen 1 , Rong Huang 1 , Xing-Han Yun 1 , Tian-Hui Hao 1 , Sheng-Jiao Yan 1
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A novel protocol for the construction of highly functionalized bipyrimidine derivatives 4 and 5 from 3-formyl-chromones, ethyl 2-(pyridine-2-yl)acetate derivatives, and amidine hydrochlorides via an interesting and considerably complex multi-component cascade reaction was developed. The cascade reaction was manifested by refluxing a mixture of the three substrates in acetonitrile or DMF along with Cs2CO3. A series of 4,5-dihydro-[4,5′-bipyrimidin]-6(1H)-ones (DBPMOs) 4 was constructed regioselectively in suitable to excellent yields. Moreover, intermediates 4 then underwent a novel, metal- and oxidant-free cascade reaction to produce a series of [4,5′-bipyrimidin]-6(1H)-ones (BPMOs) 5. The formation of the bipyrimidine derivatives 4–5 was enabled by the formation of five bonds and the cleavage of one bond in one pot. This protocol can be used in the synthesis of functionalized bipyrimidine derivatives via a multi-component one-pot cascade reaction rather than multi-step reactions, which is suitable for both combinatorial and parallel syntheses of bipyrimidine derivatives.
中文翻译：
3-甲酰基色酮的多组分级联反应：4,5-二氢-[4,5'-联嘧啶]-6(1H)-one衍生物的高选择性合成
开发了一种通过有趣且相当复杂的多组分级联反应从 3-甲酰基色酮、2-（吡啶-2-基）乙酸乙酯衍生物和脒盐酸盐构建高度官能化的双嘧啶衍生物 4 和 5 的新方案. 通过将三种底物在乙腈或 DMF 中的混合物与 Cs 2 CO 3一起回流来证明级联反应。一系列 4,5-二氢-[4,5'-联嘧啶]-6(1 H )-ones (DBPMOs) 4 被区域选择性地构建，以达到优异的产率。此外，中间体 4 随后经历了一种新型的、无金属和无氧化剂的级联反应，产生了一系列 [4,5'-联嘧啶]-6(1 H)-ones (BPMOs) 5. 联嘧啶衍生物4-5的形成是通过形成五个键并在一锅中裂解一个键来实现的。该协议可用于通过多组分一锅级联反应而不是多步反应合成功能化双嘧啶衍生物，适用于双嘧啶衍生物的组合和平行合成。
更新日期：2021-07-13
中文翻译：
3-甲酰基色酮的多组分级联反应：4,5-二氢-[4,5'-联嘧啶]-6(1H)-one衍生物的高选择性合成
开发了一种通过有趣且相当复杂的多组分级联反应从 3-甲酰基色酮、2-（吡啶-2-基）乙酸乙酯衍生物和脒盐酸盐构建高度官能化的双嘧啶衍生物 4 和 5 的新方案. 通过将三种底物在乙腈或 DMF 中的混合物与 Cs 2 CO 3一起回流来证明级联反应。一系列 4,5-二氢-[4,5'-联嘧啶]-6(1 H )-ones (DBPMOs) 4 被区域选择性地构建，以达到优异的产率。此外，中间体 4 随后经历了一种新型的、无金属和无氧化剂的级联反应，产生了一系列 [4,5'-联嘧啶]-6(1 H)-ones (BPMOs) 5. 联嘧啶衍生物4-5的形成是通过形成五个键并在一锅中裂解一个键来实现的。该协议可用于通过多组分一锅级联反应而不是多步反应合成功能化双嘧啶衍生物，适用于双嘧啶衍生物的组合和平行合成。
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