Microwave-assisted regioselective sulfenylation of indoles under solvent- and metal-free conditions

被引:50
作者
Rahaman, Rajjakfur [1 ]
Devi, Namita [1 ]
Bhagawati, Jyoti Rekha [1 ]
Barman, Pranjit [1 ]
机构
[1] Natl Inst Technol Silchar, Dept Chem, Silchar 788010, India
关键词
CATALYZED SULFENYLATION; EFFICIENT SULFENYLATION; BISINDOLE ALKALOIDS; INHIBITORS; DISULFIDES; CHLORIDES; SULFONES; ACIDS; 3-SULFENYLATION; SUBSTITUTION;
D O I
10.1039/c5ra26425a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we report a solvent-and metal-free methodology for the sulfenylation of indoles with sulfinic acids in the absence of an external catalyst under microwave irradiation. This environmentally friendly approach offered the desired products in moderate to excellent yields in only 10 min. Several functional group tolerances were monitored under the optimized conditions.
引用
收藏
页码:18929 / 18935
页数:7
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共 80 条
[21]   Efficient Microwave-Assisted Synthesis of Unsymmetrical Disulfides [J].
Goermer, Kristina ;
Waldmann, Herbert ;
Triola, Gemma .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1811-1813
[22]   Recent developments in indole ring synthesis-methodology and applications [J].
Gribble, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075
[23]   Activation and Deactivation of a Chemical Transformation by an Electromagnetic Field: Evidence for Specific Microwave Effects in the Formation of Grignard Reagents [J].
Gutmann, Bernhard ;
Schwan, Alexander M. ;
Reichart, Benedikt ;
Gspan, Christian ;
Hofer, Ferdinand ;
Kappe, C. Oliver .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7636-7640
[24]   Mechanism of the second sulfenylation of indole [J].
Hamel, P .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :2854-2858
[25]   Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry [J].
Herrero, M. Antonia ;
Kremsner, Jennifer M. ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :36-47
[26]   Green Chemistry with a Novel 5.8-GHz Microwave Apparatus. Prompt One-Pot Solvent-Free Synthesis of a Major Ionic Liquid: The 1-Butyl-3-methylimidazolium Tetrafluoroborate System [J].
Horikoshi, Satoshi ;
Hamamura, Tomofumi ;
Kajitani, Masatsugu ;
Yoshizawa-Fujita, Masahiro ;
Serpone, Nick .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (06) :1089-1093
[27]   Practical methodologies for the synthesis of indoles [J].
Humphrey, Guy R. ;
Kuethe, Jeffrey T. .
CHEMICAL REVIEWS, 2006, 106 (07) :2875-2911
[28]   THE REACTION OF ACYLOXYSULFONIUM SALT WITH CYCLIC ENOL ETHERS - NOVEL SYNTHESIS OF VINYL SULFIDES [J].
JAIN, S ;
SHUKLA, K ;
MUKHOPADHYAY, A ;
SURYAWANSHI, SN ;
BHAKUNI, DS .
SYNTHETIC COMMUNICATIONS, 1990, 20 (09) :1315-1320
[29]   Revisiting nucleophilic substitution reactions: Microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium [J].
Ju, Yuhong ;
Kumar, Dalip ;
Varma, Rajender S. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6697-6700
[30]   Controlled microwave heating in modern organic synthesis [J].
Kappe, CO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284