RING SIZE PREFERENCE IN THE INTRAMOLECULAR CYCLIZATION OF AMINES WITH ESTERS - SYNTHESIS OF AMINO-ACID DERIVED HEXAHYDROPYRIMIDINES AND TETRAHYDROIMIDAZOLES

被引：7

作者：

BESSE, R ^{[1
]}

GARRATT, PJ ^{[1
]}

HOBBS, CJ ^{[1
]}

ROGERS, HM ^{[1
]}

SUELEIMAN, AM ^{[1
]}

WALPOLE, CSJ ^{[1
]}

WRIGGLESWORTH, R ^{[1
]}

机构：

[1] SANDOZ INST MED RES,LONDON WC1E 6BN,ENGLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(01)90077-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the sequential addition of β aminoesters and amines to diphenyl cyanocarbonimidate it has been shown that, if there is a choice, the intramolecular cyclisation of the amine to the esters gives a 5-membered rather than a 6-membered diazaheterocycle. 13C NMR and IR spectroscopic assignments were made in cases in which the ring size was unequivocal and these assignments were then used to determine the size of the ring in cyclisations in which rings of either size could be formed. A previous structural assignment has been revised on the basis of this spectroscopic analysis. A number of the newly prepared tetrahydroimidazoles and hexahydropyrimidines are conceptually derived from dipeptides. © 1990.

引用

页码：7803 / 7812

页数：10

共 10 条

[1] HYDROGEN-BONDING .9. SOLUTE PROTON DONOR AND PROTON ACCEPTOR SCALES FOR USE IN DRUG DESIGN [J].