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

页码：7952 / 7967

页数：16