Ring formation from 2-arylazo-3-aminocrotononitriles to 1,2,3[2H]-triazole-4-carbonitriles and pyrazoles by anodic oxidation

被引：7

作者：

Wei, XD ^{[1
]}

Speiser, B ^{[1
]}

机构：

[1] UNIV TUBINGEN,INST ORGAN CHEM,D-72076 TUBINGEN,GERMANY

来源：

ELECTROCHIMICA ACTA | 1997年 / 42卷 / 01期

关键词：

anodic oxidation; electrochemistry; enamines; heterocyclic ring formation; triazoles; pyrazoles;

D O I：

10.1016/0013-4686(96)00168-5

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

Arylazo substituted enamines are converted at room temperature into 2-aryl-1,2,3[2H]-triazoles by galvanostatic anodic oxidation in acetonitrile in fair yields without the use of metal ions. Pyrazoles are formed as side products. Their yield can be increased in methanol as solvent, employing potentiostatic reaction conditions. Reaction mechanisms for the formation of the products are proposed, where the triazole formation constitutes a new intramolecular pathway for the anodic oxidation of enamines, while the pyrazole formation includes the participation of a non-oxidized enamine molecule. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：73 / 79

页数：7

共 50 条

[31] Spiro[carbazole-1(2H),2′-[1,3]dithiolan]-4(3H)-one
Hokelek, T
Gunduz, H
Patir, S
Uludag, N
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 : 1297 - 1299
[32] 1,2,3 = 2,3,4: Accommodating the cladogram
Feduccia, A
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (09) : 4740 - 4742
[33] 2-benzoylspiro[1H-isoindole-1,3′-isochromene]-1′,3,4′(2H,3′H)-trione
McSweeney, N
Pratt, AC
Creaven, BS
Long, C
Howie, RA
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O2025 - O2028
[34] 4′-(4-methoxybenzoyl)-1′-methyldispiro-[indole-3(2H),2′-pyrrolodine-3′,3"(2"H)-indole]-2,2"-dione
Palani, K
Ponnuswamy, MN
Babu, ARS
Raghunathan, R
Nethaji, M
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O4260 - O4262
[35] THE FORMATION OF CYCLOPENTENONES AND 3(2H)-FURANONES FROM ACETYLENIC PRECURSORS
WILLIAMS, DR
ABBASPOUR, A
JACOBSON, RM
TETRAHEDRON LETTERS, 1981, 22 (37) : 3565 - 3568
[36] 4′-(4-chlorobenzoyl)-1′-methyldispiro-[indole-3(2H),2′-pyrrolidine-3′,3"(2"H)-indole]-2,2"-dione
Palani, K
Ponnuswamy, MN
Babu, ARS
Raghunathan, R
Nethaji, M
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O4257 - O4259
[37] 4′-(4-bromobenzoyl)-1′-methyldispiro-[indole-3(2H),2′-pyrrolidine-3′,3"(2"H)-indole]-2,2"-dione
Palani, K
Ponnuswamy, MN
Babu, ARS
Raghunathan, R
Ravikumar, K
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O4254 - O4256
[38] 2 NOVEL 2-HYDROXY-3(2H)-THIOPHENONES FROM THE REACTION BETWEEN CYSTINE AND 2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE
SHU, CK
HAGEDORN, ML
MOOKHERJEE, BD
HO, CT
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1985, 33 (04) : 638 - 641
[39] Diazoaldehyde chemistry .3. Synthesis of 4-acyl-1H-1,2,3-triazole derivatives
Sezer, O
Dabak, K
Akar, A
Anac, O
HELVETICA CHIMICA ACTA, 1996, 79 (02) : 449 - 453
[40] The synthesis of 5-amino-4-arylazo-3-methyl-1H-pyrazoles and 5-aryl-3-methylpyrazole[3,4-e][1,2,3,4]tetrazines
Yang, Bo
Lu, Yuan
Chen, Chao-Jun
Cui, Jian-Ping
Cai, Meng-Shen
DYES AND PIGMENTS, 2009, 83 (02) : 144 - 147

← 1 2 3 4 5 →