On Water Synthesis of 3-Aryl-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidines using Iodobenzene Diacetate

被引：4

作者：

Soni, Rinku ^{[1
]}

Aneja, Deepak Kumar ^{[1
]}

Sihag, Monika ^{[1
]}

Rani, Neha ^{[1
]}

Kinger, Mayank ^{[1
]}

机构：

[1] Chaudhary Bansi Lal Univ, Dept Chem, Bhiwani 127021, Haryana, India

来源：

LETTERS IN ORGANIC CHEMISTRY | 2023年 / 20卷 / 05期

关键词：

Hydrazone; hypervalent iodine reagents; heterocycles; oxidative cyclization; triazolopyrimidine; water; organic solvents; HETEROCYCLIC-COMPOUNDS; OXIDATIVE CYCLIZATION; ALS INHIBITORS; SULFONYLUREAS; NUCLEOSIDES; HYDRAZONES; DESIGN; ACID;

D O I：

10.2174/1570178620666221025160300

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and green methodology has been developed for the synthesis of 3-aryl-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidines in water. Oxidative cyclization of 4,6-dimethyl-2-pyrimidinylhydrazones of different aldehydes was achieved in good to excellent yield using iodobenzene diacetate at room temperature. High efficiency, easy work-up, short reaction time, non-toxicity of solvent and ambient temperature are the advantages of this methodology.

引用

页码：401 / 406

页数：6

共 49 条

[1] Synthesis, analgesic, and antiparkinsonian profiles of some pyridine, pyrazoline, and thiopyrimidine derivatives [J].

Abdel-Latif, Nehad A. ;

Sabry, Nermien M. ;

Mohamed, Ashraf M. ;

Abdulla, Mohamed M. .

MONATSHEFTE FUR CHEMIE, 2007, 138 (07) :715-724

[2]

Akiba K.Y., 1998, CHEM HYPERVALENT COM

[3]

Andrea R., 2014, RECENT ADV CARDIOVAS, V9, P51

[4] SYNTHESIS OF THIENOQUINOLINES .3. SYNTHESIS OF NOVEL 4-HYDRAZINO-TETRAHYDROQUINOLINO[3',2'-4,5]THIENO[3,2-D]PYRIMIDINE DERIVATIVES [J].

AWAD, IMA ;

ABDELRAHMAN, AE ;

BAKHITE, EA .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 69 (3-4) :213-218

[5] Water in organocatalytic processes: Debunking the myths [J].

Blackmond, Donna G. ;

Armstrong, Alan ;

Coombe, Vyv ;

Wells, Andrew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3798-3800

[6] THE PREPARATION OF FUSED TRIAZOLE SYSTEMS [J].

BOWER, JD ;

DOYLE, FP .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (FEB) :727-732

[7] DETECTION OF A METALLO-INTERMEDIATE AND GEOMETRICAL ISOMERIZATIONS IN AN OXIDATIVE CYCLIZATION OF A HETEROCYCLIC HYDRAZONE WITH MERCURY(II) ACETATE [J].

BUTLER, RN ;

JOHNSTON, SM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (08) :376-377

[8] A convenient new synthesis of fused 1,2,4-triazoles:: the oxidation of heterocyclic hydrazones using copper dichloride [J].

Ciesielski, M ;

Pufky, D ;

Döring, M .

TETRAHEDRON, 2005, 61 (24) :5942-5947

[9] Hypervalent-Iodine-Mediated Carbon-Carbon Bond Cleavage and Dearomatization of 9H-Fluoren-9-ols [J].

Deng, Ruixian ;

Zhan, Shuming ;

Li, Chunyu ;

Gu, Zhenhua .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (08) :3093-3098

[10]

El Ashry ESH, 2000, CURR ORG CHEM, V4, P609

← 1 2 3 4 5 →