3-Aminofuro[2,3-b]pyridines: Reaction with N-Chlorosuccinimide and Sodium Hypochlorite

被引：1

作者：

Stroganova, T. A. ^{[1
]}

Vasilin, V. K. ^{[1
]}

Shitikov, N. V. ^{[1
]}

Dmitrieva, I. G. ^{[2
]}

Krapivin, G. D. ^{[1
]}

机构：

[1] Kuban State Technol Univ, Krasnodar 350072, Russia

[2] Kuban State Agrarian Univ, Krasnodar 350044, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2024年 / 94卷 / 02期

关键词：

3-aminofuro[2,3-b]pyridines; chlorination; nucleophilic substitution; herbicide 2,4-D; antidote activity; DERIVATIVES; FUROPYRIDINES;

D O I：

10.1134/S1070363224020075

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of aminoamides of the furo[2,3-b]pyridine series with an aqueous solution of sodium hypochlorite and N-chlorosuccinimide was studied. It was found that the chlorination reaction proceeds at position 2 of the furopyridine system, leading to previously unknown 3-imino-2-chlorofuro[2,3-b]pyridine-2-carboxamides. For some synthesized compounds, nucleophilic substitution reactions were investigated. Among the obtained substances, compounds were identified that have antidote activity against 2,4-D.

引用

页码：314 / 326

页数：13

共 23 条

[1]

Al‐Refai M, 2018, European Journal of Chemistry, V9, P375, DOI [10.5155/eurjchem.9.4.375-381.1792, 10.5155/eurjchem.9.4.375-381.1792, DOI 10.5155/EURJCHEM.9.4.375-381.1792]

[2]

[Anonymous], 2004, Patent, Patent No. 2302422

[3]

Chkanikov D.I., 1973, Herbicidal Effect of 2,4-D and Other Halophenoxy Acids

[4] Synthesis of New Fused Furo- and Thienopyridines [J].

Dabaeva, V. V. ;

Baghdasaryan, M. R. ;

Paronikyan, E. G. ;

Tamazyan, R. A. ;

Ayvazyan, A. G. ;

Dashyan, Sh. Sh. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (12) :2364-2368

[5] Furo[2,3-b]pyridine-based cannabinoid-1 receptor inverse agonists: Synthesis and biological evaluation. Part 1 [J].

Debenham, John S. ;

Madsen-Duggan, Christina B. ;

Toupence, Richard B. ;

Walsh, Thomas F. ;

Wang, Junying ;

Tong, Xinchun ;

Kumar, Sanjeev ;

Lao, Julie ;

Fong, Tung M. ;

Xiao, Jing Chen ;

Huang, Cathy R-R. C. ;

Shen, Chun-Pyn ;

Feng, Yue ;

Marsh, Donald J. ;

Stribling, D. Sloan ;

Shearman, Lauren P. ;

Strack, Alison M. ;

Goulet, Mark T. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (04) :1448-1452

[6] Applications of N-chlorosuccinimide in organic synthesis [J].

Golebiewski, W. Marek ;

Gucma, Miroslaw .

SYNTHESIS-STUTTGART, 2007, (23) :3599-3619

[7] Synthesis and biological evaluation of pyrido[3′,2':4,5]furo [3,2-d]pyrimidine derivatives as novel PI3 kinase p110α inhibitors [J].

Hayakawa, Masahiko ;

Kaizawa, Hiroyuki ;

Moritomo, Hiroyuki ;

Koizumi, Tomonobu ;

Ohishi, Takahide ;

Yamano, Mayumi ;

Okada, Minoru ;

Ohta, Mitsuaki ;

Tsukamoto, Shin-ichi ;

Raynaud, Florence I. ;

Workman, Paul ;

Waterfield, Michael D. ;

Parker, Peter .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) :2438-2442

[8] Synthesis and cytotoxicity of thieno[2,3-b]pyridine and furo[2,3-b]pyridine derivatives [J].

Hung, Joy M. ;

Arabshahi, Homayon J. ;

Leung, Euphemia ;

Reynisson, Johannes ;

Barker, David .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 86 :420-437

[9] Synthesis, characterization and cytotoxicity of new nicotinonitriles and their furo[2,3-b]pyridine derivatives [J].

Ibrahim, Mohammad M. ;

Al-Refai, Mahmoud ;

Azmi, Mohamad Nurul ;

Osman, Hasnah ;

Abu Bakar, Mohamad Hafizi ;

Geyer, Armin .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (04) :715-722

[10] Reactions with N-chlorosuccinimide of various methylimidazo[1, 2-a]pyridine derivatives with electron-withdrawing group substituted at the 3-position [J].

Ikemoto, T ;

Wakimasu, M .

HETEROCYCLES, 2001, 55 (01) :99-108

← 1 2 3 →