Synthesis of Novel C6-Phosphonated Purine Nucleosides under Microwave Irradiation by SNAr−Arbuzov Reaction

Abstract

Novel C6-phosphonated purine nucleosides were obtained in good to excellent isolated yields by the simple and catalyst-free SNAr-Arbuzov reaction of trialkyl phosphite with 6-choloropurine nucleosides, including a series of nonsugar carbon nucleosides. Shorter reaction times were needed, and substantially higher yields were obtained under microwave irradiation conditions compared with conventional heating conditions.

Efficient and green synthesis of purine arabinosides via CuO catalyzed dehydrazination in tap water

“…The reaction time could be shortened to 6 h and the yield was maintained (entry 11). Other copper salts including CuSO 4 , CuCl 2 and Cu 2 O were also tested, but decreased yields were observed (entries [12][13][14]. More importantly, when the solvent changed to tap water, the cheaper and more environmentally benign solvent, the yield also was maintained which showed the good future of industrial application (entry 15).…”

“…In the context of ongoing projects on the synthesis of purine nucleosides, [11][12][13][14][15] herein, we realized the efficient synthesis of a series of arabinosides via dehydrazination reaction at a catalytic amount of CuO (route c, Scheme 2). In addition, tap water was suitable for this reaction as an environmentally benign solvent.…”

Three‐Component Reaction Using the Bestmann–Ohira Reagent: A Regioselective Synthesis of Phosphonyl Pyrazole Rings

“…3 In view of the importance of heterocycles bearing a phosphonate group, new synthetic methods that would allow straightforward access to these versatile building blocks are needed 1. 4, 5 Among the various bioactive heterocycles, the pyrazole moiety remains of great interest because of its wide applications in the pharmaceutical and agrochemical industry 6. 7 In addition, pyrazoles also play a central role in coordination chemistry 8.…”

Intermolecular C−N Cross‐Coupling Reactions Catalyzed by Tetra‐n‐butylammonium Iodide: Synthesis of Allylic N‐Heterocycles

“…Purine bases and nucleosides, as the universal units in DNA and RNA, have found broad applications in biological and pharmaceutical chemistry.R ecently,p urine derivatives as the nitrogen sourcesi nt he C(sp 3 )ÀHb ond amination have been developed. [8] In 2013, Zhu and co-workersr eported ar emarkable nBu 4 NI-catalyzed benzylic CÀHb onda mination with purined erivatives. [9] In our previous communication, nBu 4 NIcatalyzed CÀNc ross-coupling imidation reaction of C(sp 3 )ÀH bond of simple ketones and NÀHb ond in imides with tertbutyl hydroperoxide (TBHP) as an environmentally benign oxidant was described.…”