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

[41] 1,2,3-Triazolo[4,5-e]-1,2,4-triazolo[3,4-c]pyrimidines
Biagi, G
Giorgi, I
Livi, O
Manera, C
Scartoni, V
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (05) : 1195 - 1198
[42] Alkylation of 1-hydroxy-1H-[1,2,3]triazolo[4,5-e] [1,2,3,4]tetrazine 5,7-dioxide
Voronin, A. A.
Zelenov, V. P.
Churakov, A. M.
Strelenko, Yu. A.
Tartakovsky, V. A.
RUSSIAN CHEMICAL BULLETIN, 2014, 63 (02) : 475 - 479
[43] Alkylation of 1-hydroxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide
A. A. Voronin
V. P. Zelenov
A. M. Churakov
Yu. A. Strelenko
V. A. Tartakovsky
Russian Chemical Bulletin, 2014, 63 : 475 - 479
[44] SYNTHESIS OF 6-AMINO-1,2,3-TRIAZOLO[4,5-C]PYRIDIN-4(5H)ONE(8-AZA-3-DEAZAGUANINE) AND 6-AMINO-1-(BETA-D-RIBOFURANOSYL)-1,2,3-TRIAZOLO[4,5-C]PYRIDIN-4(5H)ONE(8-AZA-3-DEAZAGUANOSINE) VIA NOVEL RING-CLOSURE PROCEDURES
MEYER, RB
REVANKAR, GR
COOK, PD
EHLER, KW
SCHWEIZER, MP
ROBINS, RK
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (01) : 159 - 169
[45] Radical C-alkylation of 1-substituted 1,2,3-triazolo[4,5-c]pyridine by tertiary butyl alcohol
Yutilov, YM
Smolyar, NN
ZHURNAL ORGANICHESKOI KHIMII, 1996, 32 (09): : 1412 - 1414
[46] Synthesis and pharmacological properties of new 3-ethoxycarbonyl-11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepines
Chimirri, A
Gitto, R
Quartarone, S
Orlando, V
De Sarro, A
De Sarro, GB
FARMACO, 2002, 57 (09): : 759 - 763
[47] New Cyclopenta[4′,5′] pyrido[3′,2′:4,5]thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidines and Cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidines: Synthesis and Antimicrobial Activities
Sirakanyan, Samvel N.
Spinelli, Domenico
Geronikaki, Athina
Kartsev, Viktor G.
Hakobyan, Elmira K.
Panosyan, Henrik A.
Stepanyan, Hrachya M.
Zuppiroli, Luca
Hovakimyan, Anush A.
CURRENT ORGANIC CHEMISTRY, 2017, 21 (13) : 1227 - 1241
[48] LEAD-TETRAACETATE OXIDATION OF 1-AMINO-5-PHENYL[1,2,3]TRIAZOLO[4,5-D][1,2,3]TRIAZOLES AND 2-AMINO-5-PHENYL[1,2,3]TRIAZOLO[4,5-D][1,2,3]TRIAZOLES - SYNTHESIS OF A FUSED 1,2,3,4-TETRAZINE
KAIHOH, T
ITOH, T
YAMAGUCHI, K
OHSAWA, A
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08): : 2045 - 2048
[49] 4H-[1,2,3]-thiadiazolo[3,4-a]benzimidazoliumides
Katritzky, AR
Nikonov, GN
Tymoshenko, DO
Steel, PJ
HETEROCYCLES, 2002, 58 : 311 - 316
[50] Synthesis and antiviral and antitumor activities of 2H-[1,2,3]triazolo[4,5-d]pyrimidines and 1H-, 2H-, and 3H-[1,2,3]triazolo[4,5-d]pyrimidin-5(4H)-one-7(6H)-thiones
Islam, Rafiqul
Nagamatsu, Tomohisa
HETEROCYCLES, 2006, 68 (11) : 2387 - 2402

← 1 2 3 4 5 →