Synthesis of aryl substituted 2,4,5,6-tetrahydro-3H-1,2,4-triazepine3-thionesi/ones starting from chalcone-derived β-isothiocyanato ketones

被引：4
|
作者：
Fesenko, Anastasia A. [1 ]
Grigoriev, Mikhail S. [2 ]
Shutalev, Anatoly D. [1 ]
机构：
[1] Moscow Technol Univ, Dept Organ Chem, 86 Vernadsky Ave, Moscow 119571, Russia
[2] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, 31 Leninsky Ave, Moscow 119071, Russia
来源：
TETRAHEDRON | 2016年 / 72卷 / 49期
基金：
俄罗斯基础研究基金会;
关键词：
Isothiocyanato ketones; Thiosemicarbazides; Hydrazones; 1,2,4-Triazepine-3-thiones/ones; CYCLISIERUNG VON SAUREAMIDEN; RING EXPANSION; WITTIG REACTION; DERIVATIVES; SEMICARBAZIDE; HETEROCYCLES; COMPLEXES; ANALOGS; METHYL; ESTERS;
D O I：
10.1016/j.tet.2016.10.021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general two-step synthesis of 7-aryl substituted 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones from 1-aryl-3-isothiocyanatopropan-1-ones has been developed. The synthesis involved reaction of these isothiocyanato ketones with hydrazines followed by acid-catalyzed heterocyclization of the prepared 4(3-oxopropyl)thiosemicarbazides or their hydrazones. Triazepine-3-thiones were converted into their 3oxo analogs by oxidation with H2O2 under basic conditions. Conformations of the obtained triazepine-3thiones/ones in DMSO solution and in solid state were established using H-1 NMR spectroscopy and single crystal X-ray diffraction. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7952 / 7967
页数：16
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