Bismuth nitrate pentahydrate:: a new and environmentally benign reagent for guanidylation of N-benzoylthioureas

被引:49
作者
Cunha, S [1 ]
de Lima, BR [1 ]
de Souza, AR [1 ]
机构
[1] Univ Fed Goias, Inst Quim, BR-74001970 Goiania, Go, Brazil
关键词
bismuth; acylguanidines; thioureas;
D O I
10.1016/S0040-4039(01)02067-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bismuth nitrate-mediated guanidylation of N-benzoylthioureas was studied. This salt proved to be an effective guanylating reagent and allowed the obtention of N-benzoyl-guanidines in good yields. The methodology described is a promising alternative to the use of toxic HgCl2 in the synthesis of polysubstituted guanidines. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:49 / 52
页数:4
相关论文
共 38 条
[1]   Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones [J].
Anderson, AM ;
Blazek, JM ;
Garg, P ;
Payne, BJ ;
Mohan, RS .
TETRAHEDRON LETTERS, 2000, 41 (10) :1527-1530
[2]   Natural guanidine derivatives [J].
Berlinck, RGS .
NATURAL PRODUCT REPORTS, 1999, 16 (03) :339-365
[3]   Natural guanidine derivatives [J].
Berlinck, RGS .
NATURAL PRODUCT REPORTS, 1996, 13 (05) :377-409
[4]   Study of N-benzoyl-activation in the HgCl2-promoted guanylation reaction of thioureas.: Synthesis and structural analysis of N-benzoyl-guanidines [J].
Cunha, S ;
Costa, MB ;
Napolitano, HB ;
Lariucci, C ;
Vencato, I .
TETRAHEDRON, 2001, 57 (09) :1671-1675
[5]   Solid-phase synthesis of N,N′-substituted acylguanidines [J].
Dodd, DS ;
Zhao, Y .
TETRAHEDRON LETTERS, 2001, 42 (07) :1259-1262
[6]   A simple chemoselective method for the deprotection of acetals and ketals using bismuth nitrate pentahydrate [J].
Eash, KJ ;
Pulia, MS ;
Wieland, LC ;
Mohan, RS .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8399-8401
[7]   Arylation with organolead and organobismuth reagents [J].
Elliott, GI ;
Konopelski, JP .
TETRAHEDRON, 2001, 57 (27) :5683-5705
[8]   Solid-phase synthesis of N-acyl-N′-alkyl/aryl disubstituted guanidines [J].
Ghosh, JK ;
Hol, WGJ ;
Fan, EK .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (06) :2161-2164
[9]  
Gomes de Souza Berlinck R, 1995, Fortschr Chem Org Naturst, V66, P119
[10]  
Greenhill J V, 1993, Prog Med Chem, V30, P203, DOI 10.1016/S0079-6468(08)70378-3