当前位置: X-MOL 学术Asian J. Org. Chem. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Pot‐Economical Synthesis of Hydroxylated Arylethenyl‐arylethynyl‐arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2017-11-17 , DOI: 10.1002/ajoc.201700504
Amit Shard 1, 2 , Rajesh Kumar 1, 2 , Danish Equbal 3 , Arun Kumar Sinha 1, 2, 3
Affiliation  

A simple, economical and one‐pot protocol is developed for construction of multiple carbon–carbon bonds having C(sp2)−C(sp2) and C(sp2)−C(sp) hybridization, as these intriguing molecular architectures exhibit significant optoelectronic and medicinal properties. To this end, a sequential reaction is devised that allows one‐pot three‐component reactions of hydroxybenzaldehydes (C6–C1 unit), halo‐phenylacetic acids (C6–C2 unit) and arylacetylenes (C6–C3 unit) resulting in the formation of highly π‐conjugated complex arylethenyl‐arylethynyl‐arenes (C6–C2–C6–C2–C6 unit) bearing a hydroxy group via sequential Perkin condensation–decarboxylation–Sonogashira coupling in polyethylene glycol with microwave irradiation. The process avoids protection–deprotection manipulations, generates CO2 and H2O as by‐products and is successfully extended for the efficient construction of a wide series of novel aliphatic/alicyclic/(hetero)aromatic arylethenyl‐arylethynyl‐arenes with pendant hydroxy functionality, which could undergo further chemical modification to achieve target biological and physical properties.

中文翻译:

通过顺序脱羧Perkin-Sonogashira反应的羟化芳基乙烯基-芳基乙炔基芳烃的锅经济合成

开发了一种简单,经济且一锅的方案,用于构建具有C(sp 2)-C(sp 2)和C(sp 2)-C(sp)杂化的多个碳-碳键,因为这些有趣的分子结构表现出显着的光电和药用特性。为此,连续的反应被设计,其允许羟基苯甲醛的一锅三组分反应(C 6 -C 1单元),卤代苯乙酸(C 6 -C 2单元)和arylacetylenes(C 6 -C 3单元)导致形成高度π共轭的复杂芳基乙烯基-芳基乙炔基芳烃(C 6 –C 2 –C6 –C 2 –C 6单元)通过在微波辐射下在聚乙二醇中进行的Perkin缩合-脱羧-Sonogashira偶联而带有羟基。该过程避免了保护-脱保护操作,产生了副产品CO 2和H 2 O,并成功地扩展了用于新型含侧链羟基官能团的脂族/脂环族/(杂)芳族芳基乙烯基-芳基乙炔基芳烃的有效构造的范围。 ,可以对其进行进一步的化学修饰以实现目标生物学和物理性质。
更新日期:2017-11-17
down
wechat
bug