A new microwave-assisted, three-component reaction of 5-aminopyrazole-4-carboxylates: Selective synthesis of substituted 5-aza-9-deaza-adenines

被引：16
作者：
Lim, Felicia Phei Lin [1 ]
Halcovitch, Nathan R. [2 ]
Tiekink, Edward R. T. [3 ]
Dolzhenko, Anton, V [1 ,4 ]
机构：
[1] Monash Univ Malaysia, Sch Pharm, Jalan Lagoon Selatan, Bandar Sunway 47500, Selangor Darul, Malaysia
[2] Univ Lancaster, Dept Chem, Lancaster LA1 4YB, England
[3] Sunway Univ, Sch Sci & Technol, Res Ctr Crystalline Mat, Bandar Sunway 47500, Selangor Darul, Malaysia
[4] Curtin Univ, Fac Hlth Sci, Curtin Hlth Innovat Res Inst, Sch Pharm, GPO Box U1987, Perth, WA 6845, Australia
来源：
TETRAHEDRON | 2018年 / 74卷 / 15期
关键词：
Pyrazole; Triazine; Purine isostere; Pyrazolo[1,5-a][1,3,5]triazine; Multicomponent reaction; Dynamic NMR spectroscopy; 5-AMINO-4,5-DIHYDROPYRAZOLO 3,4-D PYRIMIDIN-4-ONES; ONE-POT; MULTICOMPONENT SYNTHESIS; ISOMERIC SYSTEMS; INHIBITORS; PURINE; KINASE; ROSCOVITINE; ROTATION; NMR;
D O I：
10.1016/j.tet.2018.02.054
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 5-aza-9-deaza- analogues of purine was effectively prepared using highly selective annulation of 1,3,5-triazine ring onto 5-aminopyrazole-4-carboxylates via a one-pot, multicomponent, microwave-assisted approach. The products were obtained in good yields and high purity. This catalyst-free method was demonstrated to be scalable and highly reproducible in different microwave reactors. Some structural features of the prepared compounds were studied in details using dynamic NMR spectroscopy and X-ray crystallography. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1868 / 1879
页数：12
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