Synthesis of symmetrical and unsymmetrical ureas using unsymmetrical diaryl carbonates

被引:24
作者
Freer, R [1 ]
McKillop, A [1 ]
机构
[1] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND
关键词
D O I
10.1080/00397919608003622
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Appropriately substituted unsymmetrical diaryl carbonates react smoothly with primary amines to give the carbamates derived by nucleophilic displacement of the less electron rich aromatic substituent. Subsequent treatment of the carbamates with primary and secondary amines gives either symmetrical or unsymmetrical ureas in excellent yield and the overall process can be carried out as a ''one pot'' operation. Acetonitrile is the preferred solvent and addition of DBU facilitates the carbamate --> urea transformation.
引用
收藏
页码:331 / 349
页数:19
相关论文
共 8 条
[1]  
BARCELO G, 1986, SYNTHESIS-STUTTGART, P627
[2]   MASS SPECTROMETRY IN STRUCTURAL AND STEREOCHEMICAL PROBLEMS .130. A STUDY OF ELECTRON IMPACT INDUCED MIGRATORY APTITUDES [J].
BROWN, P ;
DJERASSI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (11) :2711-&
[3]   ESTER AMINOLYSIS - STRUCTURE-REACTIVITY RELATIONSHIP AND RATE-DETERMINING STEP IN AMINOLYSIS OF SUBSTITUTED DIPHENYL CARBONATES [J].
GRESSER, MJ ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (21) :6963-6970
[4]  
HEGARTY AF, 1979, COMPREHENSIVE ORGANI, V2, P1084
[5]  
IZDEBSKI J, 1989, SYNTHESIS-STUTTGART, P423
[6]   A SAFE AND EFFICIENT METHOD FOR PREPARATION OF N,N'-UNSYMMETRICALLY DISUBSTITUTED UREAS UTILIZING TRIPHOSGENE [J].
MAJER, P ;
RANDAD, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1937-1938
[7]  
Sandler S.R., 1971, ORGANIC FUNCTIONAL G, V2, P135
[8]   AROMATISCHE ALDEHYDE AUS KOHLENWASSERSTOFFEN UBER DIE CARBONSAURE-N-METHYLANILIDE - ALDEHYDE AUS CARBONSAUREN .6. MITTEIL [J].
WEYGAND, F ;
MITGAU, R .
CHEMISCHE BERICHTE-RECUEIL, 1955, 88 (02) :301-308