Preparation of 5-diaminomethylenebarbiturates by barbituric acid addition to carbodiimides

被引:22
作者
Jursic, BS [1 ]
Douelle, F [1 ]
Stevens, ED [1 ]
机构
[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
关键词
barbituric acid; 5-diaminomethylenebarbiturates; immuno-modulating agents;
D O I
10.1016/S0040-4020(03)00489-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Through NMR spectroscopic monitoring of barbituric acid addition to carbodiimide, a general synthetic procedure for the preparation of 5-diaminomethylenebarbiturates (DABA) was developed. This procedure is very simple and applicable to the preparation of large quantities of DABA derivatives. Through an X-ray structural study of one of the DABA derivatives, it was established that these compounds have an ylide-type structure with strong charge separation within the molecule. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3427 / 3432
页数:6
相关论文
共 19 条
[1]   COMMON EFFECT OF PHOSPHINES AND CARBON TETRACHLORIDE ON AMMONIA (DERIVATIVES) .4. NEW CARBODIIMIDE SYNTHESIS [J].
APPEL, R ;
KLEINSTU.R ;
ZIEHN, KD .
CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (04) :1335-&
[2]  
Ashkinazi R. I., 1999, Int. Patent., Patent No. [WO 99/25699, 9925699]
[3]  
De Belin JY, 2001, WO 01/93841, pA2, Patent No. 0193841
[4]   Synthesis and spectroscopic characterization of 5-diaminomethylidene barbiturates [J].
Figueroa-Villar, JD ;
Clemente, FC ;
da Silva, ACC .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (02) :247-254
[5]   Chemo-immunotherapy and chemo-adoptive immunotherapy of cancer [J].
Gomez, GG ;
Hutchison, RB ;
Kruse, CA .
CANCER TREATMENT REVIEWS, 2001, 27 (06) :375-402
[6]  
GOMPPER R, 1985, CHEM BER, V98, P1391
[7]   Unique charge-separated pyridinium-barbituric acid zwitterions [J].
Jursic, BS ;
Neumann, DM ;
Moore, Z ;
Stevens, ED .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2372-2374
[8]   Preparation of dibarbiturates of oxindole by condensation of isatin and barbituric acid derivatives [J].
Jursic, BS ;
Stevens, ED .
TETRAHEDRON LETTERS, 2002, 43 (32) :5681-5683
[9]   A simple method for knoevenagel condensation of α,β-conjugated and aromatic aldehydes with barbituric acid [J].
Jursic, BS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) :655-657
[10]   Anticancer activity for 4,4′-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) analogues and their abilities to interact with lymphoendothelial cell surface markers [J].
Morgan, LR ;
Jursic, BS ;
Hooper, CL ;
Neumann, DM ;
Thangaraj, K ;
LeBlanc, B .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (23) :3407-3411