Hydrazinolysis of 3-R-[1,2,4]Triazino[2,3-c]quinazolin-2-ones. Synthetic and Theoretical Aspects

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• 作者：Tetiana Yu. Sergeieva ; Oleksiy Yu. Voskoboynik ; Sergiy I. Okovytyy ; Sergiy I. Kovalenko ; Svitlana V. Shishkina ; Oleg V. Shishkin ; Jerzy Leszczynski
• 刊名：Journal of Physical Chemistry A
• 出版年：2014
• 出版时间：March 13, 2014
• 年：2014
• 卷：118
• 期：10
• 页码：1895-1905
• 全文大小：515K
• 年卷期：v.118,no.10(March 13, 2014)
• ISSN：1520-5215

文摘

It has been shown that heating of 3-R-[1,2,4]triazino[2,3-c]quinazolin-2-ones with 5-fold excess of hydrazine hydrate in propanol-2 gave the corresponding 3-(2-aminophenyl)-6-R-1,2,4-triazin-5-ones with high yields. The mechanism of the reaction has been proposed based on the results of theoretical investigation at B3LYP and MP2 levels of theory. According to calculations, an attack of the hydrazine molecule on the C₆鈺怤₇ double bond leads to ring-opening with N₅鈥揅₆ bond cleavage. The process continues by addition of the second nucleophile molecule and elimination of the formazan fragment through a series of transformations that yield the target product.