A New One-Pot Three-Component Synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under Microwave Irradiation

被引：9

作者：

Shahari, Muhammad Syafiq Bin ^{[1
]}

Junaid, Ahmad ^{[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] Purdue Univ, Dept Med Chem & Mol Pharmacol, W Lafayette, IN 47907 USA

[3] Sunway Univ, Res Ctr Crystalline Mat, Sch Med & Life Sci, 5 Jalan Univ, Bandar Sunway 47500, Selangor Darul, Malaysia

[4] Curtin Univ, Fac Hlth Sci, Sch Pharm & Biomed Sci, Curtin Hlth Innovat Res Inst, GPO Box U1987, Perth, WA 6845, Australia

来源：

SYNTHESIS-STUTTGART | 2021年 / 53卷 / 14期

关键词：

triazines; multicomponent reactions; microwave-assisted synthesis; dehydrogenative aromatization; antiproliferative activity;

D O I：

10.1055/a-1401-2795

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) into the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amities. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-[3,4-dihydroisoquinolin-2(1H)-yl]-4- phenyl-1,3,5-triazin-2-amine.

引用

页码：2457 / 2468

页数：12

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