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

页码：1868 / 1879

页数：12

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