A facile, environmentally benign sulfonamide synthesis in water

被引：97

作者：

Deng, Xiaohu ^{[1
]}

Mani, Neelakandha S. ^{[1
]}

机构：

[1] Johnson & Johnson Pharmaceut Res & Dev LLC, Dept Drug Discovery, San Diego, CA 92121 USA

来源：

GREEN CHEMISTRY | 2006年 / 8卷 / 09期

关键词：

D O I：

10.1039/b606127c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile, environmentally benign synthesis of sulfonamides under dynamic pH control in aqueous media is described. This methodology uses equimolar amounts of amino compounds and arylsulfonyl chlorides and omits the use of organic bases. Isolation of products involves only filtration after acidification. Excellent yields and purity were obtained without further purification.

引用

页码：835 / 838

页数：4

共 25 条

[1]

Andersen K.K., 1979, COMPREHENSIVE ORGANI, V3

[2] Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids [J].

Caddick, S ;

Wilden, JD ;

Judd, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (04) :1024-1025

[3]

Frost CG, 2002, SYNLETT, P1928

[4]

GOLDENBERG C, 1977, EUR J MED CHEM, V12, P81

[5] Novel sulfonate derivatives: Potent antimitotic agents [J].

Gwaltney, SL ;

Imade, HM ;

Li, Q ;

Gehrke, L ;

Credo, RB ;

Warner, RB ;

Lee, JY ;

Kovar, P ;

Frost, D ;

Ng, SC ;

Sham, HL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1671-1673

[6] PREPARATION OF NONSYMMETRICAL PARA-BENZOQUINONE DIIMINES FOR EVALUATION AS PROTEIN CLEAVAGE REAGENTS [J].

HOLMES, TJ ;

LAWTON, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19) :3146-3150

[7] Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors [J].

Hu, WH ;

Guo, ZR ;

Chu, FM ;

Bai, AP ;

Yi, X ;

Cheng, GF ;

Li, J .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) :1153-1160

[8] N-sulfonylbenzotriazoles as advantageous reagents for C-sulfonylation [J].

Katritzky, AR ;

Abdel-Fattah, AAA ;

Vakulenko, AV ;

Tao, H .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9191-9197

[9] Benzenesulfonyl chloride with primary and secondary amines in aqueous media - Unexpected high conversions to sulfonamides at high pH [J].

King, JF ;

Gill, MS ;

Ciubotaru, P .

CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (09) :1525-1535

[10] PH OPTIMIZATION OF NUCLEOPHILIC REACTIONS IN WATER [J].

KING, JF ;

RATHORE, R ;

LAM, JYL ;

GUO, ZR ;

KLASSEN, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3028-3033

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