ChemInform Abstract: Synthesis and Stereochemistry of Stereoisomeric 1,3‐Oxazino‐ and 1,3‐ Thiazino(4,3‐a)isoquinolines.

Abstract

Synthesis and Stereochemistry of Stereoisomeric 1,3-Oxazinoand 1,3-Thiazino(4,3-a)isoquinolines.-Reaction of the 1-(dihydroxypropyl)tetrahydroisoquinolines (I) with the isothiocyanates (II) gives the 2-thiocarbamoyl derivatives (III). S-Methylation with methyl iodide followed by cyclization upon treatment with KOH produces the oxazinoisoquinolines (IV), whereas acid-mediated ring closure gives the thiazinoisoquinolines (V). The oxazinoisoquinolines (VII) or (VIII) are prepared by reaction of (I) with the aldehydes (VI). Single crystal X-ray analysis of (VIIc) is reported (space group P21n, Z = 4). -(FUELOEP, F.; BERNATH, G.; EL-GHARIB, M. S.; KOBOR, J.; SOHAR, P.; PELCZER, I.; ARGAY, G.; KALMAN, A.; Magy. Kem. Foly. 97 (1991) 6, 229-237; Szent-Gyoergyi Albert Orvostud. Egyetem, Gyogyszereszi Vegytani Intezet, 6701 Szeged, Hung.; HU)