Practical synthesis of unsymmetrical ureas from isopropenyl carbamates

被引：62

作者：

Gallou, I ^{[1
]}

Eriksson, M ^{[1
]}

Zeng, XZ ^{[1
]}

Senanayake, C ^{[1
]}

Farina, V ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 17期

关键词：

D O I：

10.1021/jo0507643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A very convenient method for the synthesis of unsymmetrical ureas is described, based on isopropenyl carbamates. The synthetic efficiency of traditional methods for urea formation, such as use of phosgene or alkyl and aryl carbamates, is limited by the formation of symmetrical urea side products or reaction reversibility. Isopropenyl carbamates react with amines cleanly and irreversibly and give unsymmetrical ureas in high yield and purity. This method is ideal for the rapid synthesis of compound libraries.

引用

页码：6960 / 6963

页数：4

共 43 条

[1] Conversion of carbonimidodithioates into unsymmetrical di- and tri-substituted ureas including urea dipeptides
Anbazhagan, M
Deshmukh, ARAS
Rajappa, S
[J]. TETRAHEDRON LETTERS, 1998, 39 (21) : 3609 - 3612
[2] SYNTHESIS OF N,N'-DISUBSTITUTED UREAS FROM CARBAMATES
BASHA, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (21) : 2525 - 2526
[3] An efficient new protocol for the formation of unsymmetrical tri- and tetrasubstituted ureas
Batey, RA
Santhakumar, V
Yoshina-Ishii, C
Taylor, SD
[J]. TETRAHEDRON LETTERS, 1998, 39 (35) : 6267 - 6270
[4] GENERATION OF SIMPLE ENOLS IN AQUEOUS-SOLUTION FROM ALKALI-METAL ENOLATES - SOME CHEMISTRY OF ISOBUTYRALDEHYDE ENOL
CHIANG, Y
KRESGE, AJ
WALSH, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) : 6314 - 6320
[5] DEAGUIRRE I, 1989, B SOC CHIM BELG, V98, P19
[6] 1-Phenyl-5-pyrazolyl ureas: Potent and selective p38 kinase inhibitors
Dumas, J
Hatoum-Mokdad, H
Sibley, R
Riedl, B
Scott, WJ
Monahan, MK
Lowinger, TB
Brennan, C
Natero, R
Turner, T
Johnson, JS
Schoenleber, R
Bhargava, A
Wilhelm, SM
Housley, TJ
Ranges, GE
Shrikhande, A
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (18) : 2051 - 2054
[7] Discovery of a new class of p38 kinase inhibitors
Dumas, J
Sibley, R
Riedl, B
Monahan, MK
Lee, W
Lowinger, TB
Redman, AM
Johnson, JS
Kingery-Wood, J
Scott, WJ
Smith, RA
Bobko, M
Schoenleber, R
Ranges, GE
Housley, TJ
Bhargava, A
Wilhelm, SM
Shrikhande, A
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (18) : 2047 - 2050
[8] RUTHENIUM-CATALYZED SYNTHESIS OF SYMMETRICAL N,N'-DIALKYLUREAS DIRECTLY FROM CARBON-DIOXIDE AND AMINES
FOURNIER, J
BRUNEAU, C
DIXNEUF, PH
LECOLIER, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) : 4456 - 4458
[9] Synthesis of symmetrical and unsymmetrical ureas using unsymmetrical diaryl carbonates
Freer, R
McKillop, A
[J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (02) : 331 - 349
[10] A novel and efficient method for the Pd-catalysed oxidative carbonylation of amines to symmetrically and unsymmetrically substituted ureas
Gabriele, B
Mancuso, R
Salerno, G
Costa, M
[J]. CHEMICAL COMMUNICATIONS, 2003, (04) : 486 - 487

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