Mason Stephen J, Hake Jen L, Nairne James, Cummins W Jon, Balasubramanian Shankar
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
J Org Chem. 2005 Apr 15;70(8):2939-49. doi: 10.1021/jo0479415.
We report here a series of studies that explore solid-phase methodologies for the synthesis of various cyanine dyes. The scope of the previously reported catch-and-release method using sulfonyl chloride resin(1) has now been extended to include pentamethine and water-soluble cyanine dyes. We also report a new and chemically distinct synthetic strategy, employing the stepwise attack of heterocyclic carbon nucleophiles on immobilized polyene-chain precursors, allowing the clean synthesis of hydrophobic and hydrophilic trimethine and pentamethine dyes from more easily obtained starting materials. Overall, both approaches appear to be robust and versatile strategies to delivering a wide range of cyanine-based dyes in high purity.
我们在此报告了一系列探索用于合成各种菁染料的固相方法的研究。此前报道的使用磺酰氯树脂的捕获与释放方法(1)的范围现已扩展至包括五甲川和水溶性菁染料。我们还报告了一种全新且化学性质不同的合成策略，该策略采用杂环碳亲核试剂对固定化多烯链前体进行逐步进攻，从而能够从更容易获得的起始原料干净利落地合成疏水和亲水的三甲川和五甲川染料。总体而言，这两种方法似乎都是能够以高纯度提供多种基于菁的染料的强大且通用的策略。
