Synthesis of 1,3,4-trisubstituted isoquinolines by iodine-mediated electrophilic cyclization of 2-alkynyl benzyl azides
Synthesis of 1,3,4-trisubstituted isoquinolines by iodine-mediated electrophilic cyclization of 2-alkynyl benzyl azides
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DOI：
10.1002/anie.200701392
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发表时间：
2007-01-01
影响因子：
16.6
通讯作者：
Yamamoto, Yoshinori
中科院分区：
文献类型：
--
作者：
Fischer, Dirk;Tomeba, Hisamitsu;Yamamoto, Yoshinori
异喹啉是一类重要的生物碱，通常存在于天然产物中。[1]它们的生物活性导致它们经常被用作药物化合物的结构单元，[2]作为过渡金属催化剂的手性配体，[3]以及有机发光二极管（OLED）中的铱络合物。[4]A对于精细天然产物的合成以及对于最终应用的化合物的生物和/或物理性质的微调，非常需要这类杂环的通用和灵活的方法。虽然已经开发了许多方法来合成异喹啉，但经典的方法如Pomernanz-Fritsch反应有相当大的缺点，例如使用强酸和高温，[5]这不适合敏感的底物。近年来，已经开发了新的过渡金属催化的反应以从苯乙炔底物合成取代的异喹啉（方案1）。[6]这些反应被证明是
Isoquinolines are an important class of alkaloids commonly found in natural products.[1] Their biological activities have resulted in them often being used as building blocks in pharmaceutical compounds,[2] as chiral ligands for transitionmetal catalysts,[3] and their iridium complexes in organic lightemitting diodes (OLEDs).[4]A general and flexible approach to this class of heterocycles is highly desirable for the syntheses of delicate natural products as well as for the fine-tuning of the biological and/or physical properties of the compounds for final application. Although many ways have been developed to synthesize isoquinolines, classical methods such as the Pomernanz–Fritsch reaction have considerable drawbacks, for example, the use of strong acids and elevated temperature,[5] which are not suitable for sensitive substrates. In recent years, new transition-metal-catalyzed reactions have been developed to synthesize substituted isoquinolines from phenylacetylene substrates (Scheme 1).[6] These reactions have proven to be