A Facile One-Pot Synthesis of 3-Imidazolyl 1,2,4-Triazoles and 1,2,4-Oxadiazolones

被引：7

作者：

Dias, Alice M. ^{[1
]}

Cabral, Isabel M. ^{[1
]}

Vila-Cha, A. Sofia ^{[1
]}

Cunha, Daniela P. ^{[1
]}

Senhoraes, Nadia ^{[1
]}

Nobre, Sandra M. ^{[1
]}

Sousa, Cristina E. ^{[1
]}

Proenca, M. Fernanda ^{[1
]}

机构：

[1] Univ Minho, Dept Quim, P-4710057 Braga, Portugal

来源：

SYNLETT | 2010年 / 18期

关键词：

heterocycles; cyclization; ring closure; imidazole; 1,2,4-triazole; 1,2,4-oxadiazole; EFFICIENT; 6-CYANOPURINES; MANNICH; BASES;

D O I：

10.1055/s-0030-1258820

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-(5-Aminoimidazol-4-yl)-1,2,4-triazol-3-ones were obtained under mild experimental conditions from 5-amino-4-(N-ethoxycarbonyl) cyanoformimidoyl imidazoles and hydrazine in a rapid one-pot reaction. When hydroxylamine hydrochloride was used, in the presence of base, the corresponding 1,2,4-oxadiazol-5ones were isolated. An equally fast reaction occurred when 5-amino-4-(N-acetyl/benzoyl) cyanoformimidoyl imidazoles were combined with hydrazine to give 5-(5-aminoimidazol-4-yl)-1,2,4-triazoles.

引用

收藏

页码：2792 / 2796

页数：5

相关论文

共 39 条

[1] Design, synthesis and molecular modeling study of acylated 1,2,4-triazole-3-acetates with potential anti-inflammatory activity [J].

Abdel-Megeed, Ashraf M. ;

Abdel-Rahman, Hamdy A. ;

Alkaramany, Gamal-Eldien S. ;

El-Gendy, Mahmoud A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (01) :117-123

[2] Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines [J].

Al-Azmi, A ;

Booth, BL ;

Carpenter, RA ;

Carvalho, A ;

Marrelec, E ;

Pritchard, RG ;

Proença, MFJRP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (20) :2532-2537

[3] Synthesis and SAR evaluation of 1,2,4-triazoles as A2A receptor antagonists [J].

Alanine, A ;

Anselm, L ;

Steward, L ;

Thomi, S ;

Vifian, W ;

Groaning, MD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (03) :817-821

[4] SYNTHESIS OF 4-DISUBSTITUTED AND 5-DISUBSTITUTED 1-BENZYLIMIDAZOLES, IMPORTANT PRECURSORS OF PURINE ANALOGS [J].

ALVES, MJ ;

PROENCA, MFJRP ;

BOOTH, BL .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (02) :345-350

[5] (Z)-N3-(2-AMINO-1,2-DICYANOVINYL)FORMAMIDRAZONE - A PRECURSOR IN THE SYNTHESIS OF 1,5-DIAMINOIMIDAZOLES AND 6-CARBAMOYL-1,2-DIHYDROPURINES [J].

ALVES, MJ ;

BOOTH, BL ;

FREITAS, AP ;

PROENCA, MFJRP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (07) :913-917

[6] Synthesis of 6-cyanopurines and the isolation and X-ray structure of novel 2H-pyrroles [J].

Alves, MJ ;

Carvalho, MA ;

Proenca, MFJRP ;

Booth, BL ;

Pritchard, RG .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (03) :739-743

[7] One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate [J].

Amarasinghe, Kande K. D. ;

Maier, Matthew B. ;

Srivastava, Anil ;

Gray, Jeffrey L. .

TETRAHEDRON LETTERS, 2006, 47 (22) :3629-3631

[8] Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities [J].

Bayrak, Hacer ;

Demirbas, Ahmet ;

Demirbas, Neslihan ;

Karaoglu, Senguel Alpay .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (11) :4362-4366

[9] Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities [J].

Bayrak, Hacer ;

Demirbas, Ahmet ;

Karaoglu, Senguel Alpay ;

Demirbas, Neslihan .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) :1057-1066

[10] Multi-gram scale mercury-free synthesis of optically pure 3,4,5-trisubstituted 1,2,4-triazoles using silver benzoate [J].

Bibian, Mathieu ;

Blayo, Anne-Laure ;

Moulin, Aline ;

Martinez, Jean ;

Fehrentz, Jean-Alain .

TETRAHEDRON LETTERS, 2010, 51 (19) :2660-2663

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