Synthesis of dihalo-substituted analogues of Troger's base from ortho- and meta-substituted anilines

被引：66

作者：

Hansson, A ^{[1
]}

Jensen, J ^{[1
]}

Wendt, OF ^{[1
]}

Wärnmark, K ^{[1
]}

机构：

[1] Lund Univ, Dept Chem, S-22100 Lund, Sweden

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 16期

关键词：

Troger's base; halogens; anilines; X-ray diffraction; supramolecular chemistry;

D O I：

10.1002/ejoc.200300144

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

For the first time, ortho- and meta-halo-substituted anilines were successfully condensed with formaldehyde to dihalo-substituted analogues of Troger's base. By using paraformaldehyde and TFA, yields of 2-85% of these potential supramolecular building blocks were obtained. Even the inconceivable achievement of condensing anilines unsubstituted in para-position to analogues of Troger's base was successful. Adding our present results to our previous, makes it now possible to synthesize analogues of Troger's base halo-substituted in almost any desired position in each of its two aromatic rings. In addition the first X-ray structure of a dihalo-substituted analogue of Troger's base, 3,9-dibromo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (17), is presented. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

引用

页码：3179 / 3188

页数：10

共 22 条

[1] Enantiospecific recognition of DNA sequences by a proflavine Troger base [J].