Stereochemical studies, 145. Saturated heterocycles, 152. Preparation and conformational analysis of stereoisomeric 1,6,7,11b- tetrahydro-2 H [1,3]oxazino [4,3-a]isoquinolin-4-one derivatives

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Abstract

Starting from 1- [bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline 3a, trifunctional 1,2,3,4-tetrahydroisoquinolines were synthetized. From the N-ethoxycarbonyl derivative of 3a, (r-11b,c-1)-1-hydroxymethyl- (8) and (r-11b,t-1)-1-chloromethy1-9,10-dimethoxy-1,6,7,llb--tetrahydro-2H1,3]oxazino[4,3-a] isoquinolin-4-one (9) were formed in unexpected reactions. High-resolution NMR revealed that the tetrahydroisoquino-line-fused C-1 epimer oxazinone derivatives 8 and 9 have different conformations in solution. The first X-ray diffraction evidence of the presence of two different conformations of oxazinoisoquinolines 8 and 9 in the solid state is provided.

Original languageEnglish
Pages (from-to)4039-4048
Number of pages10
JournalTetrahedron
Volume46
Issue number11
DOIs
Publication statusPublished - 1990

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Tetrahydroisoquinolines
X-Ray Diffraction
Conformations
Derivatives
Nuclear magnetic resonance
X ray diffraction
heliamine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{b678238abb19495ca79e98ba8fded642,
title = "Stereochemical studies, 145. Saturated heterocycles, 152. Preparation and conformational analysis of stereoisomeric 1,6,7,11b- tetrahydro-2 H [1,3]oxazino [4,3-a]isoquinolin-4-one derivatives",
abstract = "Starting from 1- [bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline 3a, trifunctional 1,2,3,4-tetrahydroisoquinolines were synthetized. From the N-ethoxycarbonyl derivative of 3a, (r-11b,c-1)-1-hydroxymethyl- (8) and (r-11b,t-1)-1-chloromethy1-9,10-dimethoxy-1,6,7,llb--tetrahydro-2H1,3]oxazino[4,3-a] isoquinolin-4-one (9) were formed in unexpected reactions. High-resolution NMR revealed that the tetrahydroisoquino-line-fused C-1 epimer oxazinone derivatives 8 and 9 have different conformations in solution. The first X-ray diffraction evidence of the presence of two different conformations of oxazinoisoquinolines 8 and 9 in the solid state is provided.",
author = "L. L{\'a}z{\'a}r and F. F{\"u}l{\"o}p and G. Dombi and G. Bern{\'a}th and G. Argay and A. K{\'a}lm{\'a}n",
year = "1990",
doi = "10.1016/S0040-4020(01)90539-3",
language = "English",
volume = "46",
pages = "4039--4048",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "11",

}

TY - JOUR

T1 - Stereochemical studies, 145. Saturated heterocycles, 152. Preparation and conformational analysis of stereoisomeric 1,6,7,11b- tetrahydro-2 H [1,3]oxazino [4,3-a]isoquinolin-4-one derivatives

AU - Lázár, L.

AU - Fülöp, F.

AU - Dombi, G.

AU - Bernáth, G.

AU - Argay, G.

AU - Kálmán, A.

PY - 1990

Y1 - 1990

N2 - Starting from 1- [bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline 3a, trifunctional 1,2,3,4-tetrahydroisoquinolines were synthetized. From the N-ethoxycarbonyl derivative of 3a, (r-11b,c-1)-1-hydroxymethyl- (8) and (r-11b,t-1)-1-chloromethy1-9,10-dimethoxy-1,6,7,llb--tetrahydro-2H1,3]oxazino[4,3-a] isoquinolin-4-one (9) were formed in unexpected reactions. High-resolution NMR revealed that the tetrahydroisoquino-line-fused C-1 epimer oxazinone derivatives 8 and 9 have different conformations in solution. The first X-ray diffraction evidence of the presence of two different conformations of oxazinoisoquinolines 8 and 9 in the solid state is provided.

AB - Starting from 1- [bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline 3a, trifunctional 1,2,3,4-tetrahydroisoquinolines were synthetized. From the N-ethoxycarbonyl derivative of 3a, (r-11b,c-1)-1-hydroxymethyl- (8) and (r-11b,t-1)-1-chloromethy1-9,10-dimethoxy-1,6,7,llb--tetrahydro-2H1,3]oxazino[4,3-a] isoquinolin-4-one (9) were formed in unexpected reactions. High-resolution NMR revealed that the tetrahydroisoquino-line-fused C-1 epimer oxazinone derivatives 8 and 9 have different conformations in solution. The first X-ray diffraction evidence of the presence of two different conformations of oxazinoisoquinolines 8 and 9 in the solid state is provided.

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U2 - 10.1016/S0040-4020(01)90539-3

DO - 10.1016/S0040-4020(01)90539-3

M3 - Article

AN - SCOPUS:4244007062

VL - 46

SP - 4039

EP - 4048

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 11

ER -