Novel syntheses of N-pivot lariat diaza-crown ethers from 4,13-bis(benzotriazolylmethyl)-4,13-diaza-1,7,10,16-tetraoxacyclooctadecane

被引:20
作者
Katritzky, AR
Belyakov, SA
Sorochinsky, AE
Steel, PJ
Schall, OF
Gokel, GW
机构
[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH,NEW ZEALAND
[2] WASHINGTON UNIV,SCH MED,DEPT MOL BIOL & PHARMACOL,ST LOUIS,MO 63110
关键词
D O I
10.1021/jo961099o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4,13-Bis(benzotriazolylmethyl)-4,13-diaza-1,7,10,16-tetraoxacyclooctadecane (6) was synthesized as a versatile intermediate in the preparation of bis(lariats) of diaza-18-crown-6. N,N'-Bis(umbelliferon-8-ylmethyl) derivative 8, bis(lariats) with terminal unsaturated groups (11c,e), ester functionalities (11d), N,N'-di-beta-aralkyl derivatives (11a,b), and gamma-oxy-substituted (13, 14) and gamma-amino-substituted (17-19) propylene-side-armed derivatives were thus prepared in moderate to excellent yields. The X-ray structure of bis(lariat) 6 and stability constants for several of the complexes of bis(lariats), derivatives of 6, with metal cations are discussed.
引用
收藏
页码:7585 / 7592
页数:8
相关论文
共 47 条
[42]   FURTHER ADVANCES IN THE CHEMISTRY OF MANNICH-BASES [J].
TRAMONTINI, M ;
ANGIOLINI, L .
TETRAHEDRON, 1990, 46 (06) :1791-1837
[43]   THE SYNTHESIS AND BINDING-PROPERTIES OF BIBRACCHIAL LARIAT ETHERS [J].
WANG, DF ;
GE, YH ;
HU, HW ;
YU, KB ;
ZHOU, ZG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (10) :685-687
[44]   STRUCTURES OF 3 COMPLEXES WITH THE HOST DIAZA-18-CROWN-6 [J].
WATSON, WH ;
NAGL, A ;
KASHYAP, RP .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :800-803
[45]   1-1 AND 1-2 COMPLEXES BETWEEN DIAZA-18-CROWN-6 AND 2,7-DIHYDROXYNAPHTHALENE [J].
WATSON, WH ;
NAGL, A ;
EDUOK, E .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :303-306
[46]  
WATSON WH, 1988, ACTA CRYSTALLOGR C, V44, P1449
[47]   PEPTIDE SIDE-ARM DERIVATIVES OF LARIAT ETHERS AND BIBRACCHIAL LARIAT ETHERS - SYNTHESES, CATION BINDING-PROPERTIES, AND SOLID-STATE STRUCTURAL DATA [J].
WHITE, BD ;
MALLEN, J ;
ARNOLD, KA ;
FRONCZEK, FR ;
GANDOUR, RD ;
GEHRIG, LMB ;
GOKEL, GW .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :937-947