Debenzorutekarpin szarmazekok szintezise reaktivitasa

Translated title of the contribution: Synthesis and reactivity of debenzorutaecarpine derivatives

József Kökösi, János Almási, Árpád Kiss, Péter Forgó, Zsolt Böcskei, Miklós Fehér, István Hermecz

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A series of 7,12-dihydropyrimido[1',2';1,2]pyrido[3,4-b]indol-4(6H)- ones was prepared by Fischer indolization of 9-arylhydrazono-6,7,8,9- tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones. Quantumchemical calculations (ab initio and AM1) indicate that position 3 of 7,12-dihydro- pyrimido[1',2';1,2]pyrido[3,4b]indol-4(6H)-one can be involved in electrophilic substitutions, while position 2 is sensitive towards nucleophilic attack. Bromination of 6-methyl-7,12- dihydropyrimido[1',2';1,2]pyrido[3,4-b]indol-4(6H)-one (16) with bromine afforded 3-bromo derivative (25), which was reacted with cyclic amines to give 2-amino-7,12-dihydro-pyrimido[1',2';1,2]pyrido[3,4-b]indol4(6H)-ones (26-30) in an addition-elimination reaction. Vielsmeier-Haack formylation of compound (16) give 12-formyl (31) and 3,12-diforinyl (32) derivatives (an N- formyl-1-aza derivative of nauclefidine alkaloid (34) at 60 °C and 100 °C, respectively. 3,12-dformyl compound (32) was oxidized to 3-carboxyl derivative (33). The quaternary salt (35), obtained from compound (16) with dimethyl sulphate, suffered a ring opening on the action of aqueous sodium hydroxide. The new compounds have been characterized by elemental analyses uv, 1H nmr and in some cases by 13C ruler, CD spectra and X-ray investigations.

Translated title of the contributionSynthesis and reactivity of debenzorutaecarpine derivatives
Original languageHungarian
Pages (from-to)135-146
Number of pages12
JournalActa pharmaceutica Hungarica
Volume69
Issue number3
Publication statusPublished - Jun 1 1999

ASJC Scopus subject areas

  • Pharmaceutical Science

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