One-Pot Synthesis of Azobenzene Derivatives by Oxidation of 2,3-Dihydrobenzothiadiazines

被引:3
作者
Cannazza, Giuseppe [1 ]
Perrone, Serena [2 ]
Rosato, Francesca [2 ]
D'Accolti, Lucia [3 ]
Parenti, Carlo [1 ]
Troisi, Luigino [2 ]
机构
[1] Univ Modena & Reggio Emilia, Dipartimento Sci Vita, I-41125 Modena, Italy
[2] Univ Salento, Dipartimento Sci & Tecnol Biol & Ambientali, I-73100 Lecce, Italy
[3] Univ Bari Aldo Moro, Dipartimento Chim, I-70126 Bari, Italy
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 07期
关键词
azo compounds; sulfonamides; oxidation; ring opening; imines; ALLOSTERIC MODULATORS; STABILITY;
D O I
10.1055/s-0033-1338587
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An oxidative route to N-substituted sulfonamidic azobenzene derivatives is reported. A mechanism, based on a rationalization of previous findings, is proposed. This simple one-pot method could be adapted to the synthesis of a range of substituted sulfonylazobenzenes with potential applications in the pharmaceutical and industrial fields.
引用
收藏
页码:962 / 966
页数:5
相关论文
共 23 条
[11]   Epimerization and hydrolysis of 3,6-dimethyl-2,3,5,6-tetrahydro[1,2,4]thiadiazino[6,5,4-hi]indole 1,1-dioxide [J].
Carrozzo, Marina M. ;
Cannazza, Giuseppe ;
Battisti, Umberto ;
Braghiroli, Daniela ;
Troisi, Luigino ;
Parenti, Carlo .
JOURNAL OF CHROMATOGRAPHY A, 2010, 1217 (52) :8136-8145
[12]   Quantitative analysis of acetylcholine in rat brain microdialysates by liquid chromatography coupled with electrospray ionization tandem mass spectrometry [J].
Carrozzo, Marina M. ;
Cannazza, Giuseppe ;
Pinetti, Diego ;
Di Viesti, Vittoria ;
Battisti, Umberto ;
Braghiroli, Daniela ;
Parenti, Carlo ;
Baraldi, Mario .
JOURNAL OF NEUROSCIENCE METHODS, 2010, 194 (01) :87-93
[13]   NITROXIDE-CATALYZED OXIDATION OF ALCOHOLS USING META-CHLOROPERBENZOIC ACID - NEW METHOD [J].
CELLA, JA ;
KELLEY, JA ;
KENEHAN, EF .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (12) :1860-1862
[14]   THE OXIDATION OF AMINES WITH PERACETIC ACID [J].
EMMONS, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (20) :5528-5530
[15]   Oxidation of anilines with hydrogen peroxide and selenium dioxide as catalyst [J].
Gebhardt, Christin ;
Priewisch, Beate ;
Irran, Elisabeth ;
Rueck-Braun, Karola .
SYNTHESIS-STUTTGART, 2008, (12) :1889-1894
[16]   Optical switches for remote and noninvasive control of cell signaling [J].
Gorostiza, Pau ;
Isacoff, Ehud Y. .
SCIENCE, 2008, 322 (5900) :395-399
[17]   Azobenzenes-synthesis and carbohydrate applications [J].
Hamon, Florian ;
Djedaini-Pilard, Florence ;
Barbot, Francis ;
Len, Christophe .
TETRAHEDRON, 2009, 65 (49) :10105-10123
[18]   MECHANISMS OF OXIDATION OF ANILINE AND RELATED COMPOUNDS IN BASIC SOLUTION [J].
KONAKA, R ;
KURUMA, K ;
TERABE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (07) :1801-&
[19]   Azodioxy-carbonyl compounds by oxidation of cyclic imines with m-CPBA [J].
Perrone, Serena ;
Pilati, Tullio ;
Rosato, Francesca ;
Salomone, Antonio ;
Videtta, Valeria ;
Troisi, Luigino .
TETRAHEDRON, 2011, 67 (11) :2090-2095
[20]   Chloro-Substituted 3-Alkylamino-4H-1,2,4-benzothiadiazine 1,1-Dioxides as ATP-Sensitive Potassium Channel Activators: Impact of the Position of the Chlorine Atom on the Aromatic Ring on Activity and Tissue Selectivity [J].
Pirotte, Bernard ;
de Tullio, Pascal ;
Nguyen, Quynh-Anh ;
Somers, Fabian ;
Fraikin, Pierre ;
Florence, Xavier ;
Wahl, Philip ;
Hansen, John Bondo ;
Lebrun, Philippe .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) :147-154