TBD-catalysed solventless synthesis of symmetrically N,N′-substituted ureas from primary amines and diethyl carbonate

被引：57

作者：

Ballini, R

Fiorini, D

Maggi, R

Righi, P

Sartori, G

Sartorio, R

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

[2] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

[3] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

GREEN CHEMISTRY | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1039/b301951a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Symmetrically N,N'-substituted ureas were obtained from primary amines in very good yields under solvent-less conditions using diethyl carbonate (DEC) as the carbonylation reagent and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as the base catalyst. The products are precipitated directly from the reaction mixture after a volatile organic compound (VOC) free aqueous work-up. The catalyst can be recovered and reused.

引用

收藏

页码：396 / 398

页数：3

相关论文

共 16 条

[1] Halogen-free process for the conversion of carbon dioxide to urethanes by homogeneous catalysis [J].

Abla, M ;

Choi, JC ;

Sakakura, T .

CHEMICAL COMMUNICATIONS, 2001, (21) :2238-2239

[2] MCM-41-TBD as a new, efficient, supported heterogeneous catalyst for the synthesis of thioureas [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Maggi, R ;

Righi, P ;

Sartori, G ;

Sartorio, R .

TETRAHEDRON LETTERS, 2002, 43 (47) :8445-8447

[3] Selected syntheses of ureas through phosgene substitutes [J].

Bigi, F ;

Maggi, R ;

Sartori, G .

GREEN CHEMISTRY, 2000, 2 (04) :140-148

[4] Reaction of aliphatic amines with acetoacetanilide in the presence of zeolite catalyst.: Solvent-free synthesis of symmetric N,N′-dialkylureas [J].

Bigi, F ;

Frullanti, B ;

Maggi, R ;

Sartori, G ;

Zambonin, E .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1004-1006

[5] Catalytic activity of MCM-41-TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate [J].

Carloni, S ;

De Vos, DE ;

Jacobs, PA ;

Maggi, R ;

Sartori, G ;

Sartorio, R .

JOURNAL OF CATALYSIS, 2002, 205 (01) :199-204

[6] Chemically reversible organogels: Aliphatic amines as "latent" gelators with carbon dioxide [J].

George, M ;

Weiss, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10393-10394

[7] DISCOVERY OF A NOVEL CLASS OF POTENT HIV-1 PROTEASE INHIBITORS CONTAINING THE (R)-(HYDROXYETHYL) UREA ISOSTERE [J].

GETMAN, DP ;

DECRESCENZO, GA ;

HEINTZ, RM ;

REED, KL ;

TALLEY, JJ ;

BRYANT, ML ;

CLARE, M ;

HOUSEMAN, KA ;

MARR, JJ ;

MUELLER, RA ;

VAZQUEZ, ML ;

SHIEH, HS ;

STALLINGS, WC ;

STEGEMAN, RA .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (02) :288-291

[8] ACAT INHIBITORS AS ANTIATHEROSCLEROTIC AGENTS - COMPOUNDS AND MECHANISMS [J].

MATSUDA, K .

MEDICINAL RESEARCH REVIEWS, 1994, 14 (03) :271-305

[9] A new catalyst for the synthesis of N,N-biphenylurea from aniline and dimethyl carbonate [J].

Nagaraju, N ;

Kuriakose, G .

GREEN CHEMISTRY, 2002, 4 (03) :269-271

[10] Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block [J].

Ono, Y .

APPLIED CATALYSIS A-GENERAL, 1997, 155 (02) :133-166