Electrochemical Synthesis of Sulfonamide Derivatives Based on the Oxidation of 2,5-Diethoxy-4-Morpholinoaniline in the Presence of Arylsulfinic Acids

被引：20

作者：

Beiginejad, Hadi ^{[1
]}

Nematollahi, Davood ^{[2
]}

机构：

[1] Malayer Univ, Fac Sci, Dept Chem, Malayer, Iran

[2] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838683, Iran

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 13期

关键词：

EFFICIENT METHOD; N; N-DIALKYL-P-PHENYLENEDIAMINES;

D O I：

10.1021/jo500812d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Some new sulfonamide derivatives were synthesized in aqueous solutions via anodic oxidation of 2,5-diethoxy-4-morpholinoaniline in the presence of arylsulfinic acids using a commercial carbon anode. In addition, the formation mechanism of the products was discussed. The obtained data show that the electrogenerated quinone diimine undergoes a Michael-type addition reaction with arylsulfinic acids to yield the respective sulfonamide derivatives. In this work, two different types of products (mono- and disulfone derivatives) in the same precursor could be isolated just by controlling the exerted potentials.

引用

页码：6326 / 6329

页数：4

共 50 条

[31] Electrochemical oxidation of 4-(piperazin-1-yl)phenols in the presence of indole derivatives: The unique regioselectivity in the synthesis of highly conjugated bisindolyl-p-quinone derivatives
Amani, Amene
Khazalpour, Sadegh
Nematollahi, Davood
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2012, 670 : 36 - 41
[32] Electrochemical synthesis of [1,2,4]oxadiazol-3-one derivatives:: anodic oxidation of N-amidoimidates
Tapsoba, I
Adhoum, N
Ben Khoud, ML
Boujlel, K
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2003, 553 : 21 - 25
[33] An Efficient Synthesis of Thio- and Thiazoloquinazolinones by the Electrochemical Oxidation of Catechols in the Presence of 2-Mercapto-4(3H)-quinazolinone
Fakhari, Ali Reza
Hasheminasab, Kobra
Ahmar, Hamid
Alizadeh, Abdolali
SYNTHESIS-STUTTGART, 2008, (24): : 3963 - 3966
[34] Mechanistic study of electrochemical oxidation of o-dihydroxybenzenes in the presence of 4-hydroxy-1-methyl-2(1H)-quinolone -: Application to the electrochemical synthesis
Moghaddam, AB
Kobarfard, F
Fakhari, AR
Nematollahi, D
Davarani, SSH
ELECTROCHIMICA ACTA, 2005, 51 (04) : 739 - 744
[35] Synthesis and evaluation of 2,5-furan, 2,5-thiophene and 3,4-thiophene-based derivatives as CXCR4 inhibitors (vol 181, 111562, 2019)
Gaines, Theresa
Garcia, Francisco
Virani, Saniya
Liang, Zhongxing
Yoon, Younghyoun
Oum, Yoon Hyeun
Shim, Hyunsuk
Mooring, Suazette Reid
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2023, 261
[36] Synthesis and Electrochemical Properties of 2,5-Disubstituted 1,4-Bis(4,5-diphenyl-1H-imidazol-2-yl)benzene Derivatives
Chugunov, D. B.
Okina, E. V.
Timonina, A. S.
Klimaeva, L. A.
Selivanova, Yu. M.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (07) : 1222 - 1227
[37] Synthesis and Electrochemical Properties of 2,5-Disubstituted 1,4-Bis(4,5-diphenyl-1H-imidazol-2-yl)benzene Derivatives
D. B. Chugunov
E. V. Okina
A. S. Timonina
L. A. Klimaeva
Yu. M. Selivanova
Russian Journal of Organic Chemistry, 2020, 56 : 1222 - 1227
[38] Efficient synthesis, spectroscopic characterization and DFT based studies of novel 1-amide 4-sulfonamide-1,2,3-triazole derivatives
Bonyad, Sarvenaz Rouhi
Mirjafary, Zohreh
Saeidian, Hamid
Rouhani, Morteza
JOURNAL OF MOLECULAR STRUCTURE, 2019, 1197 : 164 - 170
[39] Electrochemical study of catechols in the presence of 2-thiazoline-2-thiol: application to electrochemical synthesis of new 4,5-dihydro-1,3-thiazol-2-ylsulfanyl-1,2-benzenediol derivatives
Fakhari, A. R.
Hosseiny Davarani, S. S.
Ahmar, H.
Makarem, S.
JOURNAL OF APPLIED ELECTROCHEMISTRY, 2008, 38 (12) : 1743 - 1747
[40] Electrochemical study of catechols in the presence of 2-thiazoline-2-thiol: application to electrochemical synthesis of new 4,5-dihydro-1,3-thiazol-2-ylsulfanyl-1,2-benzenediol derivatives
A. R. Fakhari
S. S. Hosseiny Davarani
H. Ahmar
S. Makarem
Journal of Applied Electrochemistry, 2008, 38 : 1743 - 1747

← 1 2 3 4 5 →