Chemical & Pharmaceutical Bulletin ( IF 1.7 ) Pub Date : 2021-09-01 , DOI: 10.1248/cpb.c21-00380 Toshitaka Shoji 1 , Kosuke Fukushima 2 , Takayuki Menjo 2 , Yoichi Yamada 3 , Tomonori Hanasaki 2 , Kotaro Kikushima 1 , Naoko Takenaga 4 , Toshifumi Dohi 1
Functionalized nucleobases are utilized in a wide range of fields; therefore, the development of new synthesis methods is essential for their continued application. With respect to the C6-arylation of halopurines, which possess a substituent at the N7-position, only a small number of successful cases have been reported, which is predominately a result of large steric hinderance effects. Herein, we report efficient and metal-free C6-arylations and SNAr reactions of N7-substituted chloropurines in aromatic and heteroatom nucleophiles promoted by triflimide (Tf2NH) in fluoroalcohol.
Fullsize Image中文翻译:
Triflimide 促进的卤代嘌呤的亲核 C-芳基化以获取 N7-取代的嘌呤联芳基
功能化的核碱基被用于广泛的领域;因此,开发新的合成方法对其继续应用至关重要。对于在N 7位具有取代基的卤嘌呤的C 6芳基化,仅报道了少量成功案例,这主要是大空间位阻效应的结果。在此,我们报告了由氟代醇中的三氟甲磺酸酯 (Tf 2 NH)促进的芳香族和杂原子亲核试剂中N 7取代的氯嘌呤的高效且无金属的C 6 -芳基化和S N Ar 反应。
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