Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles

被引：28

作者：

Piccionello, Antonio Palumbo ^{[1
]}

Guarcello, Annalisa ^{[1
]}

Buscemi, Silvestre ^{[1
]}

Vivona, Nicolo ^{[1
]}

Pace, Andrea ^{[1
]}

机构：

[1] Univ Palermo, Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 24期

关键词：

FLUORINATED HETEROCYCLIC-COMPOUNDS; RING TRANSFORMATIONS; EXPEDIENT ROUTE; 5-PERFLUOROALKYL-1,2,4-OXADIAZOLES; DERIVATIVES; DESIGN; ATTACK;

D O I：

10.1021/jo102049r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino-1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity is demonstrated also in the absence of C(5)-linked electron-withdrawing groups.

引用

收藏

页码：8724 / 8727

页数：4

相关论文

共 35 条

[1] Practical route for N,O-heteroatom interchange in 3,5-disubstituted-4-nitroisoxazoles [J].

Adamo, Mauro F. A. ;

Donati, Donato ;

Sarti-Fantoni, Piero ;

Buccioni, Arianna .

TETRAHEDRON LETTERS, 2008, 49 (06) :941-944

[2] Modular syntheses of isoxazoloazepinones and pyrazoloazepinones [J].

Adamo, Mauro F. A. ;

Duffy, Eleanor F. ;

Donati, Donato ;

Sarti-Fantoni, Piero .

TETRAHEDRON, 2007, 63 (12) :2684-2688

[3] Modular synthesis of isoxazolopyridones and pyrazolopyridones [J].

Adamo, Mauro F. A. ;

Duffy, Eleanor F. ;

Donati, Donato ;

Sarti-Fantoni, Piero .

TETRAHEDRON, 2007, 63 (09) :2047-2052

[4] Design and synthesis of 4H-3-(2-phenoxy)phenyl-1,2,4-triazole derivatives as benzodiazepine receptor agonists [J].

Akbarzadeh, T ;

Tabatabai, SA ;

Khoshnoud, MJ ;

Shafaghi, B ;

Shafiee, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (05) :769-773

[5] Fluorinated heterocyclic compounds.: An effective strategy for the synthesis of fluorinated Z-oximes of 3-perfluoroalkyl-6-phenyl-2H-1,2,4-triazin5-ones via a ring-enlargement reaction of 3-benzoyl-5-perfluoroalkyl-1,2,4-oxadiazoles and hydrazine [J].

Buscemi, S ;

Pace, A ;

Piccionello, AP ;

Macaluso, G ;

Vivona, N ;

Spinelli, D ;

Giorgi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3288-3291

[6] Fluorinated heterocyclic compounds - The first example of an irreversible ring-degenerate rearrangement on five-membered heterocycles by attack of an external bidentate nucleophile [J].

Buscemi, S ;

Pace, A ;

Pibiri, I ;

Vivona, N ;

Lanza, CZ ;

Spinelli, D .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (05) :974-980

[7] Fluorinated heterocyclic compounds. An expedient route to 5-perfluoroalkyl-1,2,4-triazoles via an unusual hydrazinolysis of 5-perfluoroalkyl-1,2,4-oxadiazoles: First examples of an ANRORC-like reaction in 1,2,4-oxadiazole derivatives [J].

Buscemi, S ;

Pace, A ;

Pibiri, I ;

Vivona, N ;

Spinelli, D .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :605-608

[8]

Buscemi S, 2002, HETEROCYCLES, V57, P811

[9] PHOTOCHEMICAL BEHAVIOR OF SOME 1,2,4-OXADIAZOLE DERIVATIVES [J].

BUSCEMI, S ;

CICERO, MG ;

VIVONA, N ;

CARONNA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1313-1315

[10] Five- to six-membered ring-rearrangements in the reaction of 5-perfluoroalkyl-1,2,4-oxadiazoles with hydrazine and methylhydrazine [J].

Buscemi, Silvestre ;

Pace, Andrea ;

Piccionello, Antonio Palumbo ;

Pibiri, Ivana ;

Vivona, Nicolo ;

Giorgi, Gianluca ;

Mazzanti, Andrea ;

Spinelli, Domenico .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8106-8113

← 1 2 3 4 →