A convenient method for the synthesis of substituted thioureas

被引:48
作者
Maddani, Mahagundappa [1 ]
Prabhu, Kandikere Ramaiah [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
D O I
10.1016/j.tetlet.2007.07.212
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient method for the synthesis of substituted thioureas by the reaction of primary amines with molybdenum dialkyl dithiocarbamates has been developed. Primary amines on reaction with 0.5 equiv of molybdenum xanthate produce the corresponding thioureas in moderate to good yields in short times. Similar reactions with propargylamine or 2-aminoethanol produce cyclic thiaoxazolidine and oxazolidine derivatives, respectively. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7151 / 7154
页数:4
相关论文
共 45 条
[1]   Direct synthesis of isothiocyanates from isonitriles by molybdenum-catalyzed sulfur transfer with elemental sulfur [J].
Adam, W ;
Bargon, RM ;
Bosio, SG ;
Schenk, WA ;
Stalke, D .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7037-7041
[2]   One-pot synthesis of N-allylthioureas using supported reagents [J].
Aoyama, T ;
Murata, S ;
Nagata, Y ;
Takido, T ;
Kodomari, M .
TETRAHEDRON LETTERS, 2005, 46 (29) :4875-4878
[3]   Molybdenum-oxo chemistry in various aspects of oxygen atom transfer processes [J].
Arzoumanian, H .
COORDINATION CHEMISTRY REVIEWS, 1998, 178 :191-202
[4]   Multiplicity of reaction pathways in the processes of oxygen transfer to secondary amines by Mo(VI) and W(VI) peroxo complexes [J].
Ballistreri, FP ;
Barbuzzi, EGM ;
Tomaselli, GA ;
Toscano, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6381-6387
[5]   A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: A strategy for diversity amplification [J].
Batey, RA ;
Powell, DA .
ORGANIC LETTERS, 2000, 2 (20) :3237-3240
[6]   Synthesis of tetrahydronaphthyl thioureas as potent appetite suppressants [J].
Bhandari, K ;
Srivastava, S ;
Shankar, G .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) :4189-4196
[7]   A dithioxo-bishydroxylaminomolybdenum complex as sulfur and nitrogen transfer reagent.: Synthesis of thioureas from isonitriles [J].
Byrne, JJ ;
Vallée, Y .
TETRAHEDRON LETTERS, 1999, 40 (03) :489-490
[8]   Synthesis, hypotensive and antiarrhythmic activities of 3-alkyl-1-(2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-3-naphthalenyl)ureas or thioureas and their guanidine analogues [J].
Chalina, EG ;
Chakarova, L .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (12) :975-983
[9]   Simple preparation of nitroso benzenes and nitro benzenes by oxidation of anilines with H2O2 catalysed with molybdenum salts [J].
Defoin, A .
SYNTHESIS-STUTTGART, 2004, (05) :706-710
[10]   Synthetic analogues and reaction systems relevant to the molybdenum and tungsten oxotransferases [J].
Enemark, JH ;
Cooney, JJA .
CHEMICAL REVIEWS, 2004, 104 (02) :1175-1200