Facile and Versatile Synthesis of Alkyl and Aryl Isothiocyanates by Using Triphosgene and Cosolvent

被引:18
作者
Liu, Pengfei [1 ]
Li, Chunyan [1 ]
Zhang, Jingwei [1 ]
Xu, Xiaoyong [1 ]
机构
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China
基金
国家高技术研究发展计划(863计划); 中国国家自然科学基金;
关键词
Amines; co-solvent; dehydrosulfurization; isothiocyanates; triphosgene; CELLS; PROTEINS; REAGENTS;
D O I
10.1080/00397911.2013.783600
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH3)(2)CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
引用
收藏
页码:3342 / 3351
页数:10
相关论文
共 23 条
[1]   A new method for the synthesis of isothiocyanates from dithiocarbamates or alkyl amines using chlorosilanes as decomposition reagents [J].
Bian, Gaofeng ;
Qiu, Huayu ;
Jiang, Jianxiong ;
Wu, Jirong ;
Lai, Guoqiao .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (03) :503-508
[2]   A one-pot preparation of isothiocyanates from amines using two phosgene substitutes:: bis-(trichloromethyl) carbonate and trichloromethyl chloroformates [J].
Bian, GF ;
Shan, WG ;
Su, WK .
JOURNAL OF CHEMICAL RESEARCH, 2005, (09) :585-586
[3]   Facile synthesis of aliphatic isothiocyanates and thioureas on solid phase using peptide coupling reagents [J].
Boas, U ;
Gertz, H ;
Christensen, JB ;
Heegaard, PMH .
TETRAHEDRON LETTERS, 2004, 45 (02) :269-272
[4]   MEMBRANE PROTEINS RELATED TO ANION PERMEABILITY OF HUMAN RED BLOOD-CELLS .2. EFFECTS OF PROTEOLYTIC-ENZYMES ON DISULFONIC STILBENE SITES OF SURFACE PROTEINS [J].
CABANTCHIK, ZI ;
ROTHSTEIN, A .
JOURNAL OF MEMBRANE BIOLOGY, 1974, 15 (03) :227-248
[5]   Triphosgene: An efficient catalyst for synthesis of isothiocyanates [J].
Chaskar, A. C. ;
Yewale, S. ;
Bhagat, R. ;
Langi, B. P. .
SYNTHETIC COMMUNICATIONS, 2008, 38 (12) :1972-1975
[6]   Novel Synthesis of Anthelmintic Drug 4-Isothiocyanato-4'-nitrodiphenyl Ether and Its Analogs [J].
Chaskar, A. C. ;
Bandgar, B. P. ;
Modhave, R. K. ;
Patil, A. B. ;
Yewale, S. .
SYNTHETIC COMMUNICATIONS, 2009, 39 (06) :992-1001
[7]  
Cotarca L, 1996, SYNTHESIS-STUTTGART, P553
[8]  
DROBNICA L, 1967, APPL MICROBIOL, V15, P710
[9]   TRIPHOSGENE, A CRYSTALLINE PHOSGENE SUBSTITUTE [J].
ECKERT, H ;
FORSTER, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (09) :894-895
[10]  
Fawzy N. M., 2009, PHARM CHEM, V1, P52