Sulfur and Nitrogen Mustard Carbonate Analogues

被引：27

作者：

Arico, Fabio ^{[1
]}

Chiurato, Matteo ^{[1
]}

Peltier, Josephine ^{[1
]}

Tundo, Pietro ^{[1
]}

机构：

[1] Univ Ca Foscari Venezia, Dipartimento Sci Ambientali Informat & Stat, I-30123 Venice, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 17期

关键词：

Mustard derivatives; Dialkyl carbonate; Nucleophilic substitution; Green chemistry; Reactive intermediates; DIMETHYL CARBONATE; AMINES;

D O I：

10.1002/ejoc.201200321

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfur and nitrogen half-mustard compounds lose their aggressive properties when the chlorine atom is replaced by a carbonate moiety. The anchimeric effect of the novel mustard carbonate analogues is investigated. The reaction follows first-order kinetics, does not need any base, and occurs with OH, NH and acidic CH nucleophiles. Most of these molecules are unexplored and might provide a novel strategy for the preparation of compounds previously not easily accessible.

引用

页码：3223 / 3228

页数：6

共 41 条

[1] Synthesis, cytotoxicity and topoisomerase inhibition properties of multifarious aminoalkylated indeno[1,2-c]isoquinolin-5,11-diones [J].

Ahn, Gang ;

Schifano-Faux, Nadege ;

Goossens, Jean-Francois ;

Baldeyrou, Brigitte ;

Couture, Axel ;

Grandclaudon, Pierre ;

Lansiaux, Amelie ;

Ryckebusch, Adina .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (08) :2259-2263

[2]

[Anonymous], 2007, Asahi Kasei Chemicals Corporation Patent, Patent No. [WO2007/34669A1, 200734669]

[3] 5-Membered N-heterocyclic compounds by dimethyl carbonate chemistry [J].

Arico, Fabio ;

Toniolo, Umberto ;

Tundo, Pietro .

GREEN CHEMISTRY, 2012, 14 (01) :58-61

[4]

Birch A. M., 2005, Patent, Patent No. [WO2005/20987, 200520987]

[5]

BLOCK E, 1978, REACTIONS ORGANOSULF, P141

[6]

Budavari S., 1989, MERCK INDEX, VEleventh

[7]

Capon B., 1976, NEIGHBORING GROUP PA

[8] Efficient Synthesis of Functionalized Aziridinium Salts [J].

Chong, Hyun-Soon ;

Song, Hyun A. ;

Dadwal, Mamta ;

Sun, Xiang ;

Sin, Inseok ;

Chen, Yunwei .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) :219-221

[9] Palladium-Catalyzed Direct and Regioselective C-H Bond Functionalization/Oxidative Acetoxylation of Indoles [J].

Choy, Pui Ying ;

Lau, Chak Po ;

Kwong, Fuk Yee .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :80-84

[10]

Cotarca L., 2003, Phosgenations - A Handbook

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