Domino reactions of tetrahydroisoquinoline difunctional compounds with 4-isothiocyanato-4-methyl-2-pentanone

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3 Citations (Scopus)

Abstract

Trans-9,10-Dimethoxy-3,3,4a-trimethyl-4,4a,6,7,11b,12-hexahydro-3H- pyrimido[6',1':2,3]-imidazo[5,1-a]isoquinoline-1(2H)-thione, cis-and trans-9,10-dimethoxy-3,3,4a-trimethyl-4,4a,6,7,12,13-hexahydro-3H, 11bH-pyrimido[6',1':2,3]pyrimido[6,1-a]isoquinoline-1(2H)-thione, trans-10,11-dimethoxy-2,2,14a-trimethyl-1,7,8,12b,13,14a-hexahydro-2H-pyrimido- [6',1':2,3][1,3,4]oxadiazino[5,4-a]isoquinoline-4(3H)-thione and trans-9,10-dimethoxy-3,3,4atrimethyl-4,4a,6a,7-tetrahydro-3H,6H,12H-pyrimido[6', 1':2,3][1,3,4]oxadiazino-[4,5-b]-isoquino-line-1(2H)-thione, previously unknown ring-annelated isoquinoline derivatives, were prepared by diastereoselective domino ring closures of tetrahydroisoquinoline diamines or hydrazinoalcohols with 4-isothiocyanato-4-methyl-2-pentanone. The relative configurations and predominant conformations of the prepared tetracycles were determined by means of NMR spectroscopy and molecular modeling calculations.

Original languageEnglish
Pages (from-to)8-16
Number of pages9
JournalArkivoc
Volume2009
Issue number12
DOIs
Publication statusPublished - 2009

Keywords

  • Diamines
  • Domino reactions
  • Hydrazinoalcohols
  • Tetrahydroisoquinolines
  • Tetrahydropyrimidine-2(1H)-thiones
  • β- Isothiocyanatoketones

ASJC Scopus subject areas

  • Organic Chemistry

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