A Microwave-Assisted One-Pot Three-Step Metal-Free [4+2] Annulation for the Sustainable Synthesis of Highly Substituted 1,2,4-Triazines

被引：1

作者：

Rubini, Daniele ^{[1
]}

Martina, Maria Grazia ^{[1
]}

Incerti, Matteo ^{[1
]}

Barbieri, Francesca ^{[1
]}

Radi, Marco ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Sci Alimenti & Farmaco DipALIFAR, Viale Sci 27 A, I-43124 Parma, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 19期

关键词：

1,2,4-Triazine; One-pot synthesis; Microwave chemistry; Hydrazones; Synthetic methods; BIOLOGICAL EVALUATION; DERIVATIVES; DESIGN;

D O I：

10.1002/ejoc.202400087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report the first microwave-assisted one-pot three-step metal-free [4+2] procedure for the synthesis of 5,6-substituted-3-hydrazinyl-1,2,4-triazines directly from commercially available aromatic and heteroaromatic ketones. The 3-hydrazinyl-1,2,4-triazine can be isolated or further elaborated, after a simple work-up, by direct condensation with different aldehydes or ketones to provide highly functionalized hydrazone-derivatives. This protocol represents a rapid, efficient, and sustainable approach for the development of new highly functionalized 1,2,4-triazine derivatives with potential biological interest. Herein we report the first microwave-assisted one-pot three-step metal-free [4+2] procedure for the synthesis of 5,6-substituted-3-hydrazinyl-1,2,4-triazines directly from commercially available aromatic and heteroaromatic ketones. Based on literature, a plausible mechanism is postulated. The 3-hydrazinyl-1,2,4-triazine can be isolated or further elaborated to provide highly functionalized hydrazone-derivatives. image

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页数：7

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