Methylation and Amination of 4H-[1,2,3]Triazolo[4,5-c][1,2,5]oxadiazole Salts

被引：2

作者：

Balabanova, S. P. ^{[1
]}

Voronin, A. A. ^{[1
]}

Churakov, A. M. ^{[1
]}

Klenov, M. S. ^{[1
]}

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

机构：

[1] Russian Acad Sci, Zelinskii Inst Organ Chem, Moscow 119991, Russia

来源：

DOKLADY CHEMISTRY | 2023年 / 512卷 / 02期

基金：

俄罗斯科学基金会;

关键词：

1,2,3-triazoles; 1,2,5-oxadiazoles; amination; methylation;

D O I：

10.1134/S0012500823600669

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methylation and amination reactions of 4 & Ncy;-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole salts (K+, Ag+, Et3NH+, DBUH+) have been studied for the first time. It has been shown that the reaction of these salts with MeI results in two methylation products: K and Et3N salts produce 4- and 5-isomers in equal amounts, while Ag and DBU salts form mainly 4-isomer. It has been found that the main amination product of K and DBU salts of 4 & Ncy;-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole with O-(p-tolylsulfonyl)hydroxylamine is 4-azido-3-amino-1,2,5-oxadiazole. A mechanism of its formation via rearrangement of 5-amino-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole has been proposed.

引用

页码：288 / 291

页数：4

共 50 条

[31] PYRIDO[2',1'-2,3]IMIDAZO[4,5-C]ISOQUINOLINE [1] AND THE ALKYLATION OF PYRIDO[2',1'-2,3]IMIDAZO[4,5-C]ISOQUINOLIN-5(6H)-ONE
PAOLINI, JP
PALOPOLI, FP
LENDVAY, LJ
HUFFMAN, J
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) : 549 - 553
[32] 7-AMINO-2,4-DIMETHYL-2H,4H-1,2,3-TRIAZOLO[4,5-C][1,2,6]THIADIAZINE 5,5-DIOXIDE
ESTEBANCALDERON, C
MARTINEZRIPOLL, M
GARCIABLANCO, S
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1982, 38 (AUG): : 2296 - 2298
[33] NEW[G]-FUSED [1,2,4]TRIAZOLO[1,5-C]PYRIMIDINES - SYNTHESIS OF PYRIDO[3,2-E] AND [4,3-E][1,2,4]TRIAZOLO[1,5-C]PYRIMIDINE, PYRIMIDO[5,4-E][1,2,4]TRIAZOLO[1,5-C]PYRIMIDINE AND [1,2,4]TRIAZOLO[1,5-C]PTERIDINE DERIVATIVES
DELGIUDICE, MR
BORIONI, A
MUSTAZZA, C
GATTA, F
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (06) : 1503 - 1507
[34] SYNTHESIS OF 2-SUBSTITUTED 4H-[1,2,4]TRIAZOLO[5,1-C][1,4]BENZOXAZINES
BIZZOZERO, N
GARANTI, L
ZECCHI, G
SYNTHESIS-STUTTGART, 1979, (11): : 909 - 910
[35] 1H-1,2,4-Triazolo-5-diazonium salts in the synthesis of novel [1,2,4]triazolo[1,5-c][1,2,4]benzotriazin-6-ols
Mohammad N. Mawlood
Andrei Yu. Potapov
Dmitriy Yu. Vandyshev
Khidmet S. Shikhaliev
Mikhail А. Potapov
Irina V. Ledenyova
Evgeniya А. Kosheleva
Chemistry of Heterocyclic Compounds, 2019, 55 : 1075 - 1079
[36] 1H-1,2,4-Triazolo-5-diazonium salts in the synthesis of novel [1,2,4]triazolo[1,5-c][1,2,4]benzotriazin-6-ols
Mawlood, Mohammad N.
Potapov, Andrei Yu
Vandyshev, Dmitriy Yu
Shikhaliev, Khidmet S.
Potapov, Mikhail A.
Ledenyova, Irina, V
Kosheleva, Evgeniya A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (11) : 1075 - 1079
[37] 1,2,3-BENZOTRIAZINES .3. SYNTHESIS OF PYRIDO[2',2'(3',2') - 4,5]IMIDAZO[1,2-C][1,2,3]BENZOTRIAZINE AND PYRIDO[3',4'(4',3') - 4,5]IMIDAZO[1,2-C][1,2,3]BENZOTRIAZINE
SPECTOR, RH
JOULLIE, MM
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (02) : 301 - &
[38] 5-[4-硝基呋咱基]-5H-[1,2,3]三唑并[4,5-c][1,2,5]呋咱内盐(NOTO)合成与表征
张叶高
王伯周
刘愆
周彦水
王锡杰
含能材料, 2010, 18 (04) : 383 - 386
[39] Cyclization of substituted 3,4-diaminopyridines into 1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxide derivatives during the nitration process
N. N. Smolyar
A. B. Vasilechko
Russian Journal of Organic Chemistry, 2010, 46 : 1219 - 1222
[40] Cyclization of Substituted 3,4-Diaminopyridines into 1H-[1,2,3]Triazolo[4,5-c]pyridine 2-Oxide Derivatives during the Nitration Process
Smolyar, N. N.
Vasilechko, A. B.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (08) : 1219 - 1222

← 1 2 3 4 5 →