Synthesis and Stereochemistry of Stereoisomeric 1,3‐Oxazino‐ and 1,3‐Thiazino[4,3‐a]isoquinolines

Ferenc Fülöp, Gäbor Bernäth, M. S. El‐Gharib, Jenö Kóbor, PÁL Sohár, István Pelczer, Gyula Argay, Alajos Kálmán

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Starting from the 6,7‐dialkoxy‐1‐[bis(hydroxymethyl)methyl]‐1,2,3,4‐tetrahydroisoquinolines 2 and 3, the 4‐imino‐substituted 1‐(hydroxymethyl)‐9,10‐dialkoxy‐2H, 4H‐1,6,11b‐tetrahydro‐1.3‐oxazino‐and ‐thiazino [4,3‐a]isoquinoline diastereomers 6a‐c, 7a‐c, 8a‐c, 9a‐c, 14, and 15 and the 4‐substituted 1,6,7,11b‐tetrahydro 1,3‐oxazino[4,3‐a]isoquinoline diastereomers 16–24 were prepared. the relative configurations and the predominant conformation of these products were determined by NMR spectroscopy and for 18 by X‐ray diffraction methods. the prepared 1,3‐oxazino[4,3‐a]isoquinoline diastereomers have predominantly trans conformations (16, 18, 22, 23), whereas cis conformations (cis‐A) prevail for 20, 21 and f24. Thus, the first evidence for either trans‐ or cis‐A conformations in 1,3‐oxazino[4,3‐a] isoquinolines is presented.

Original languageEnglish
Pages (from-to)803-809
Number of pages7
JournalChemische Berichte
Volume123
Issue number4
DOIs
Publication statusPublished - 1990

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Isoquinolines
Stereochemistry
Conformations
Nuclear magnetic resonance spectroscopy
Diffraction
isoquinoline

Keywords

  • 1,3‐Oxazino[4,3‐a]isoquinolien / 1,3‐Thiazino [4,3‐a]isoquinoline / Conformational analysis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and Stereochemistry of Stereoisomeric 1,3‐Oxazino‐ and 1,3‐Thiazino[4,3‐a]isoquinolines. / Fülöp, Ferenc; Bernäth, Gäbor; El‐Gharib, M. S.; Kóbor, Jenö; Sohár, PÁL; Pelczer, István; Argay, Gyula; Kálmán, Alajos.

In: Chemische Berichte, Vol. 123, No. 4, 1990, p. 803-809.

Research output: Contribution to journalArticle

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AU - El‐Gharib, M. S.

AU - Kóbor, Jenö

AU - Sohár, PÁL

AU - Pelczer, István

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AU - Kálmán, Alajos

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AB - Starting from the 6,7‐dialkoxy‐1‐[bis(hydroxymethyl)methyl]‐1,2,3,4‐tetrahydroisoquinolines 2 and 3, the 4‐imino‐substituted 1‐(hydroxymethyl)‐9,10‐dialkoxy‐2H, 4H‐1,6,11b‐tetrahydro‐1.3‐oxazino‐and ‐thiazino [4,3‐a]isoquinoline diastereomers 6a‐c, 7a‐c, 8a‐c, 9a‐c, 14, and 15 and the 4‐substituted 1,6,7,11b‐tetrahydro 1,3‐oxazino[4,3‐a]isoquinoline diastereomers 16–24 were prepared. the relative configurations and the predominant conformation of these products were determined by NMR spectroscopy and for 18 by X‐ray diffraction methods. the prepared 1,3‐oxazino[4,3‐a]isoquinoline diastereomers have predominantly trans conformations (16, 18, 22, 23), whereas cis conformations (cis‐A) prevail for 20, 21 and f24. Thus, the first evidence for either trans‐ or cis‐A conformations in 1,3‐oxazino[4,3‐a] isoquinolines is presented.

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