Polyfunctional macroheterocycles. 4. Synthesis and some chemical transformations of nitrogen- and sulfur-containing crown compounds with exocyclic methoxycarbonyl, cyano, and phenylethyl groups

✍ Scribed by M. G. Voronkov; V. I. Knutov; M. K. Butin

• Publisher: Springer US
• Year: 1992
• Tongue: English
• Weight: 327 KB
• Volume: 28
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00473951

✦ Synopsis

The acylation of 1,5-diamino-, 1,5-bis(2-phenylethylamino)-, and 1,5-bis(2-methoxycarbonylethylamino)-3thiapentanes with adipic and phthalic acid dichlorides, as well as oxalyl chloride, leads to, respectively, 13-, 22-, and 18-membered macroheterocycles containing exocyclic methoxycarbonyl and phenylethyl groups. The reduction by LiA1H 4 of the endocyclic amido groups and exocyclic ester or cyano groups of some nitrogen-and sulfur-containing crown compounds, which are converted to CH2NR 2, CH2OH, and CH2NH 2 groups, respectively, was studied. A macrobicyclic system containing endocyclic amido groups was synthesized, and its reduction, which leads to the corresponding CH2NR 2 derivative, was investigated.