Diversified Aminohydantoins from Ureas and Thioureas Tethered to Amides

被引：17

作者：

Bepary, Sukumar ^{[2
]}

Youn, In Kwon ^{[2
]}

Lim, Hee-Jong ^{[1
]}

Lee, Ge Hyeong ^{[1
]}

机构：

[1] Korea Res Inst Chem Technol, Taejon 305600, South Korea

[2] Pai Chai Univ, Dept Chem, Taejon 302160, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 13期

关键词：

Cyclization; Amides; Hydantoins; Nitrogen heterocycles; Carbodiimides; SOLID-PHASE SYNTHESIS; PARALLEL SYNTHESIS; DERIVATIVES; INHIBITORS;

D O I：

10.1002/ejoc.201200025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular cyclization of thioureas or ureas tethered to amides afforded 2-iminohydantoins and 2-amino-1H-imidazol-4(5H)-ones in very high yields (87100?%) regardless of the substituent (alkyls or aryls). This reaction proceeds through carbodiimides and iminium ions as intermediates. Among the reagents used to generate the carbodiimides, CBr4/Ph3P, CCl4/Ph3P, O,O'-bis(2'-pyridyl)thiocarbonate, and HgO were investigated.

引用

页码：2542 / 2548

页数：7

共 34 条

[1] LONG-ACTING DIHYDROPYRIDINE CALCIUM-ANTAGONISTS .2. 2-[2-AMINOHETEROCYCLOETHOXY]METHYL DERIVATIVES [J].

ARROWSMITH, JE ;

CAMPBELL, SF ;

CROSS, PE ;

BURGES, RA ;

GARDINER, DG .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) :562-568

[2]

Bac P, 1998, J NEUROSCI, V18, P4363

[3] A one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles [J].

Cee, Victor J. ;

Downing, Nicholas S. .

TETRAHEDRON LETTERS, 2006, 47 (22) :3747-3750

[4] ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION [J].

CHINCHILLA, R ;

NAJERA, C ;

SANCHEZAGULLO, P .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1393-1402

[5] Synthesis and structure-affinity relationships of novel small molecule natural product derivatives capable of discriminating between serotonin 5-HT1A, 5-HT2A, 5-HT2C receptor subtypes [J].

Cummings, David F. ;

Canseco, Diana C. ;

Sheth, Pratikkumar ;

Johnson, James E. ;

Schetz, John A. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (13) :4783-4792

[6] Synthesis and preliminary biological evaluation of new derivatives of the marine alkaloid leucettamine B as kinase inhibitors [J].

Debdab, Mansour ;

Renault, Steven ;

Lozach, Olivier ;

Meijer, Laurent ;

Paquin, Ludovic ;

Carreaux, Francois ;

Bazureau, Jean-Pierre .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :805-810

[7] Identification of potential glycogen kinase-3 inhibitors by structure based virtual screening [J].

Dessalew, Nigus ;

Bharatam, Prasad V. .

BIOPHYSICAL CHEMISTRY, 2007, 128 (2-3) :165-175

[8] Application of carbodiimide in heterocyclic synthesis: New facile synthesis of 2-aminoimidazolinone derivatives [J].

Ding, MW ;

Tu, HY ;

Liu, ZJ .

SYNTHETIC COMMUNICATIONS, 1997, 27 (20) :3657-3662

[9] Solid-phase synthesis of 2-aminoimidazolinones [J].

Drewry, DH ;

Ghiron, C .

TETRAHEDRON LETTERS, 2000, 41 (36) :6989-6992

[10] Cell Division Cycle 7 Kinase Inhibitors: 1H-Pyrrolo[2,3-b]pyridines, Synthesis and Structure - Activity Relationships [J].

Ermoli, Antonella ;

Bargiotti, Alberto ;

Brasca, Maria Gabriella ;

Ciavolella, Antonella ;

Colombo, Nicoletta ;

Fachin, Gabriele ;

Isacchi, Antonella ;

Menichincheri, Maria ;

Molinari, Antonio ;

Montagnoli, Alessia ;

Pillan, Antonio ;

Rainoldi, Sonia ;

Sirtori, Federico Riccardi ;

Sola, Francesco ;

Thieffine, Sandrine ;

Tibolla, Marcellino ;

Valsasina, Barbara ;

Volpi, Daniele ;

Santocanale, Corrado ;

Vanotti, Ermes .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (14) :4380-4390

← 1 2 3 4 →