Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-c][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism

被引：13

作者：

Ledenyova, I. V. ^{[1
]}

Falaleev, A. V. ^{[1
]}

Shikhaliev, Kh. S. ^{[1
]}

Ryzhkova, E. A. ^{[2
]}

Zubkov, F. I. ^{[2
]}

机构：

[1] Voronezh State Univ, Univ Skaya Pl 1, Voronezh 394006, Russia

[2] Peoples Friendship Univ Russia, Ul Miklukho Maklaya 6, Moscow 117198, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2018年 / 88卷 / 01期

关键词：

ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylate; thiourea; ANRORC rearrangement; formylation; RING CONTRACTION REACTIONS; EXPANSION; DERIVATIVES; 4-CHLOROMETHYL-1,2,3,4-TETRAHYDRO-6-METHYL-2-OXOPYRIMIDINE-5-CARBOXYLATE;

D O I：

10.1134/S1070363218010115

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylates with thiourea in dimethylformamide involves ANRORC rearrangement (Addition of the Nucleophile, Ring Opening, and Ring Closure) followed by N-formylation to give N-{5-(4-oxo-8-phenyl-1,4-dihydropyrazolo[5,1-c][1,2,4]-triazin-3-yl)-1,3-triazol-2-yl}formamides whose structure was confirmed by X-ray analysis. The reaction mechanism has been studied by HPLC/MS.

引用

页码：73 / 79

页数：7

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