Acta Chimica Sinica ›› 1983, Vol. 41 ›› Issue (8): 730-733. Previous Articles     Next Articles

Original Articles

大二环型侧向穴醚的合成

Lehe,J.M.;吴成泰;Plumere,P.   

  1. 武汉大学化学系;Le Bel Institute, Louis Pasteur Universi
  • 发布日期:1983-08-15

Synthesis of lateral macrobicyclic cryptand

LEHN,J.M.;WU CHENGTAI;PLUMERE,P.   

  • Published:1983-08-15

This paper deals with the synthesis of a new lateral macrobicyclic cryptand 2. Condensation of 2,6-di(bromomethyl)- pyridine with 3-(N-tosylamino)-methyl propionate in the presence of anhydrous K2CO3 at room temperature gave compound 6 which was hydrolyzed to 7. The latter reacted with excessive sulfonyl chloride to afford 2,6-di(4'-chloroformyl-2'-tosyl-2'-azabutyl)-pyridine 8. Pentaaza-1, 5, 13, 17, 28-dithia-20, 25-tricyclo (15, 5, 5, 1-7,11)- octacosa-7, 9, 11 (28)-triene 2 has been synthesized by the following sequence of reations. Condensation of compound 8 with 1, 7-diaza-4, 10 dithia-dodecane 5, using high dilution technique in toluene-THF at room temperature afforded 9, which was reduced by diborane in THF solution to give compound 10. Treatment of 10 with sodium anthracene in monoglyme produced compound 2.

Key words: PYRIDINE P, NITROGEN HETEROCYCLICS, MACROCYCLIC COMPOUNDS, SULFUR HETEROCYCLICS COMPOUNDS, CRYPTAND

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