NEW HIGH-YIELD SYNTHESES OF CYCLAMS USING THE CRAB-LIKE CYCLIZATION REACTION

被引:31
作者
BRADSHAW, JS
KRAKOWIAK, KE
IZATT, RM
ZAMECKAKRAKOWIAK, DJ
机构
[1] Department of Chemistry, Brigham Young University, Provo
关键词
D O I
10.1016/S0040-4039(00)88730-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new high yield method to synthesize cyclams containing one or two unsubstituted ring nitrogen atoms and with alkyl groups on the remaining ring nitrogen atoms is presented. The method consists of the ring closure reaction of a crab-like bis-α-chloroamide with a bis-secondary amine followed by reduction. The amide functions of the starting material act as protecting groups for the protons on the amide nitrogen atoms. © 1990.
引用
收藏
页码:1077 / 1080
页数:4
相关论文
共 27 条
[1]   SYNTHESIS AND CHARACTERIZATION OF TETRA-N-ALKYLATED CYCLAM LIGANDS THAT CONTAIN A FUNCTIONALIZED NITROGEN SUBSTITUENT [J].
BAREFIELD, EK ;
FOSTER, KA ;
FREEMAN, GM ;
HODGES, KD .
INORGANIC CHEMISTRY, 1986, 25 (26) :4663-4668
[2]   METAL-COMPLEXES OF 1,4,8,11-TETRAMETHYL-1,4,8,11-TETRAAZACYCLOTETRADECANE, N-TETRAMETHYLCYCLAM [J].
BAREFIELD, EK ;
WAGNER, F .
INORGANIC CHEMISTRY, 1973, 12 (10) :2435-2439
[3]   METAL-COMPLEXES WITH MACROCYCLIC LIGANDS .18. A STUDY OF STERIC EFFECTS IN THE CO-2+-COMPLEX, NI-2+-COMPLEX AND CU-2+-COMPLEX WITH 1-(2-AMINOETHYL)-4,8,11-TRIMETHYL-1,4,8,11-TETRAAZACYCLOTETRADECANE AND 1-(2-DIMETHYLAMINOETHYL)-4,8,11-TRIMETHYL-1,4,8,11-TETRAAZACYCLOTETRADECANE [J].
BASAK, AK ;
KADEN, TA .
HELVETICA CHIMICA ACTA, 1983, 66 (07) :2086-2092
[4]  
BIRNBAUM SM, 1952, J BIOL CHEM, V194, P455
[5]   CONVENIENT SYNTHESES OF N-[2-(2-HYDROXYETHOXY)ETHYL]-SUBSTITUTED POLYAZA-CROWN ETHERS AND CYCLAMS WITHOUT THE NEED FOR A HYDROXY BLOCKING GROUP [J].
BRADSHAW, JS ;
KRAKOWIAK, KE ;
IZATT, RM .
TETRAHEDRON LETTERS, 1989, 30 (07) :803-806
[6]  
BRADSHAW JS, IN PRESS J HETEROCYC
[7]   THE CHEMISTRY OF 1,4,7-TRIAZACYCLONONANE AND RELATED TRIDENTATE MACROCYCLIC-COMPOUNDS [J].
CHAUDHURI, P ;
WIEGHARDT, K .
PROGRESS IN INORGANIC CHEMISTRY, 1987, 35 :329-436
[8]  
CURTIS NF, 1968, COORDIN CHEM REV, V3, P1
[9]  
DYE JL, 1973, J ORG CHEM, V38, P1772
[10]   GENERAL ROUTES FOR THE SYNTHESIS OF MONO, DI AND TRI-N-SUBSTITUTED DERIVATIVES OF CYCLAM [J].
HELPS, IM ;
PARKER, D ;
MORPHY, JR ;
CHAPMAN, J .
TETRAHEDRON, 1989, 45 (01) :219-226