Study of N-benzoyl-activation in the HgCl2-promoted guanylation reaction of thioureas.: Synthesis and structural analysis of N-benzoyl-guanidines

被引:64
作者
Cunha, S
Costa, MB
Napolitano, HB
Lariucci, C
Vencato, I
机构
[1] Univ Fed Goias, Inst Quim, Lab Bioatividade Mol, BR-74001970 Goiania, Go, Brazil
[2] Univ Fed Goias, Inst Fis, Lab Cristalog & Mat, BR-74001970 Goiania, Go, Brazil
关键词
guanidines; thioureas; guanylation reaction; X-ray analysis;
D O I
10.1016/S0040-4020(00)01168-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this work, it is demonstrated that the benzoyl group is an activating group for thioureas in the HgCl2-guanylation reaction. Thus N-benzoyl-thioureas containing electronically neutral and even electron-withdrawing or electron-releasing substituents are converted into guanidines with reasonable yields. In addition, NMR and X-ray structural analyses were performed to understand the intra- and intermolecular features of the synthesized guanidines. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1671 / 1675
页数:5
相关论文
共 26 条
[1]   Preparation of N,N'-bis(aryl)guanidines from electron deficient amines via masked carbodiimides [J].
Barvian, MR ;
Showalter, HDH ;
Doherty, AM .
TETRAHEDRON LETTERS, 1997, 38 (39) :6799-6802
[2]   Natural guanidine derivatives [J].
Berlinck, RGS .
NATURAL PRODUCT REPORTS, 1996, 13 (05) :377-409
[3]   1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS [J].
BERNATOWICZ, MS ;
WU, YL ;
MATSUEDA, GR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2497-2502
[4]   GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].
CREMER, D ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358
[5]   Solid-phase synthesis of N,N′ substituted guanidines [J].
Dodd, DS ;
Wallace, OB .
TETRAHEDRON LETTERS, 1998, 39 (32) :5701-5704
[6]   NUCLEAR-MAGNETIC-RESONANCE STUDIES OF ANTICONVULSANT ENAMINONES [J].
EDAFIOGHO, IO ;
MOORE, JA ;
ALEXANDER, MS ;
SCOTT, KR .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 83 (08) :1155-1170
[7]  
ELIEL EL, 1994, STEREOCHEMISTRY ORGA, P550
[8]   Triurethane-protected guanidines and triflyldiurethane-protected guanidines: New reagents for guanidinylation reactions [J].
Feichtinger, K ;
Sings, HL ;
Baker, TJ ;
Matthews, K ;
Goodman, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8432-8439
[9]   Diprotected triflylguanidines: A new class of guanidinylation reagents [J].
Feichtinger, K ;
Zapf, C ;
Sings, HL ;
Goodman, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3804-3805
[10]   Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants [J].
Foster, JE ;
Nicholson, JM ;
Butcher, R ;
Stables, JP ;
Edafiogho, IO ;
Goodwin, AM ;
Henson, MC ;
Smith, CA ;
Scott, KR .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (11) :2415-2425