Reactions of N-sulfonyl-1,2,3-thiadiazole-4-carbimidamides with sulfonyl chlorides: regiospecific synthesis and structure of 2-sulfonyl-1,2,3-triazoles

被引：2

作者：

Beryozkina, Tetyana V. ^{[1
]}

Filimonov, Valeriy O. ^{[1
]}

Dianova, Lidiya N. ^{[1
]}

Slepukhin, Pavel A. ^{[2
,3
]}

Mazur, Dmitriy M. ^{[4
]}

Pospelova, Tatiana A. ^{[1
]}

Bakulev, Vasiliy A. ^{[1
,3
]}

机构：

[1] Ural Fed Univ, Dept Technol Organ Synth, 19 Mira St, Ekaterinburg 620002, Russia

[2] Ural Fed Univ, Dept Organ & Biomol Chem, 19 Mira St, Ekaterinburg 620002, Russia

[3] Russian Acad Sci, Ural Branch, Postovsky Inst Organ Synth, 22 S Kovalevskoi 20 Akad Skaya St, Ekaterinburg 620990, Russia

[4] Lomonosov Moscow State Univ, Dept Organ Chem, 1 Bldg 3 Leninskie Gory, Moscow 119992, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2019年 / 55卷 / 06期

基金：

俄罗斯基础研究基金会;

关键词：

N-sulfonyl amidines; 2-sulfonyl-1,2,3-triazoles; sulfonyl chlorides; 1,2,3-thiadiazoles; rearrangement; 4,5-FUNCTIONALIZED 1,2,3-THIADIAZOLES; 1,2,3-TRIAZOLES; NH-1,2,3-TRIAZOLES;

D O I：

10.1007/s10593-019-02494-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfonylation of 1,2,3-thiadiazolecarboxylic acid amidines in the presence of a base was found to be accompanied by the Cornforth rearrangement of the 1,2,3-thiadiazole ring into 1,2,3-triazole leading to the formation of 2-substituted 1,2,3-triazoles in high yields.

引用

页码：547 / 553

页数：7

共 18 条

[1]

[Anonymous], 2018, CAMBRIDGE STRUCTURAL

[2]

Bakulev VAR, 1995, CHEM REV, V107, P64

[3] NH-1,2,3-triazoles: synthesis and reactions with electrophilic agents [J].

Bakulev, Vasiliy A. ;

Beryozkina, Tetyana V. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (01) :4-6

[4]

Beryozkina T., 2016, SYNTHESIS-STUTTGART, P1046

[5] Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1-and 2-sulfonyl-4-azolyl-1,2,3-triazoles [J].

Beryozkina, Tetyana V. ;

Efimov, Ilya V. ;

Fabian, Walter M. F. ;

Beliaev, Nikolai A. ;

Slepukhin, Pavel A. ;

Isenov, Maxim L. ;

Dehaen, Wim ;

Lubec, Gert ;

Eltsov, Oleg S. ;

Fan, Zhijin ;

Thomas, Joice ;

Bakulev, Vasiliy A. .

TETRAHEDRON, 2015, 71 (36) :6189-6195

[6] Reactions of Malonothioamide Derivatives with Azides [J].

Dianova, L. N. ;

Berseneva, V. S. ;

El'tsov, O. S. ;

Fan, Z. -J. ;

Bakulev, V. A. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (07) :972-978

[7] Reactions of Thioacetamide Derivatives with Sulfonyl Azides: An Approach to Active-Methylene N-Sulfonylacetamidines [J].

Dianova, Lidia ;

Berseneva, Vera ;

Beryozkina, Tetyana ;

Efimov, Ilya ;

Kosterina, Maria ;

Eltsov, Oleg ;

Dehaen, Wim ;

Bakulev, Vasiliy .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (31) :6917-6923

[8] OLEX2: a complete structure solution, refinement and analysis program [J].

Dolomanov, Oleg V. ;

Bourhis, Luc J. ;

Gildea, Richard J. ;

Howard, Judith A. K. ;

Puschmann, Horst .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341

[9] A catalyst and additive-free three-component reaction of highly electrophilic azides with cyclic ketones and cycloaliphatic amines. Synthesis of novel N-heteroaryl amidines [J].

Efimov, Ilya ;

Beliaev, Nikolai ;

Beryozkina, Tetyana ;

Slepukhin, Pavel ;

Bakulev, Vasiliy .

TETRAHEDRON LETTERS, 2016, 57 (18) :1949-1952

[10] Pericyclic versus pseudopericyclic 1,5-electrocyclization of iminodiazomethanes. An ab initio and density functional theory study [J].

Fabian, WMF ;

Bakulev, VA ;

Kappe, CO .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :5801-5805

← 1 2 →