1H and 13C NMR and X-ray studies of 2- and 4-phenyl-6,7-dimethoxy-3methyl-3,4-dihydro-2H-1,3-benzothiazines [1]

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Abstract

The stereochemistry of 2- and 4-phenyl-6,7-dimethoxy-3-methyl-3,4-dihydro-2H-1,3-benzothiazine (2,6) has been studied by 1H, 13C NMR spectroscopy and X-ray diffraction. Crystals of compound 2 (C17H19NO2S) are monoclinic, space group P21/n, with a = 11.428(1), b = 10.048(1), c = 14.161(2) Å, ß = 100.00(1)°, Z = 4, Dc = 1.247 g cm-3. Crystals of 6 are orthorhombic, space group P212121 with a = 7.068(1), b = 10.857(1), c = 20.343(1) Å, Z = 4, Dc = 1.247 g cm-3. The structures are refined to R = 0.041 for 2728 reflections of 2 and R = 0.039 for 1671 reflections of 6. The results unequivocally show that the 3-N-methyl group, and the 4-phenyl group are axial, while the 2-phenyl moiety is equatorial. Comparison are made between conformations of the title compounds and those of the following 1-phenyltetrahydroisoquinolines: unnatural cryptostyline II [2, 3], crypstostyline I [4] and 2-benzyl-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-phenyl-isoquinolinium iodide [5].

Original languageEnglish
Pages (from-to)341-354
Number of pages14
JournalJournal of Molecular Structure
Volume145
Issue number3-4
DOIs
Publication statusPublished - 1986

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Iodides
X-Ray Diffraction
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
X-Rays
X rays
nuclear magnetic resonance
Crystals
Stereochemistry
Nuclear magnetic resonance spectroscopy
Conformations
x rays
X ray diffraction
stereochemistry
iodides
crystals
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
diffraction
spectroscopy

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Materials Science (miscellaneous)
  • Atomic and Molecular Physics, and Optics

Cite this

@article{cd6d360a696a441e9a4ee24fabeb815d,
title = "1H and 13C NMR and X-ray studies of 2- and 4-phenyl-6,7-dimethoxy-3methyl-3,4-dihydro-2H-1,3-benzothiazines [1]",
abstract = "The stereochemistry of 2- and 4-phenyl-6,7-dimethoxy-3-methyl-3,4-dihydro-2H-1,3-benzothiazine (2,6) has been studied by 1H, 13C NMR spectroscopy and X-ray diffraction. Crystals of compound 2 (C17H19NO2S) are monoclinic, space group P21/n, with a = 11.428(1), b = 10.048(1), c = 14.161(2) {\AA}, {\ss} = 100.00(1)°, Z = 4, Dc = 1.247 g cm-3. Crystals of 6 are orthorhombic, space group P212121 with a = 7.068(1), b = 10.857(1), c = 20.343(1) {\AA}, Z = 4, Dc = 1.247 g cm-3. The structures are refined to R = 0.041 for 2728 reflections of 2 and R = 0.039 for 1671 reflections of 6. The results unequivocally show that the 3-N-methyl group, and the 4-phenyl group are axial, while the 2-phenyl moiety is equatorial. Comparison are made between conformations of the title compounds and those of the following 1-phenyltetrahydroisoquinolines: unnatural cryptostyline II [2, 3], crypstostyline I [4] and 2-benzyl-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-phenyl-isoquinolinium iodide [5].",
author = "A. K{\'a}lm{\'a}n and G. Argay and P. Soh{\'a}r and J. Szab{\'o} and L. Fodor and G. Bern{\'a}th",
year = "1986",
doi = "10.1016/0022-2860(86)85038-4",
language = "English",
volume = "145",
pages = "341--354",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "3-4",

}

TY - JOUR

T1 - 1H and 13C NMR and X-ray studies of 2- and 4-phenyl-6,7-dimethoxy-3methyl-3,4-dihydro-2H-1,3-benzothiazines [1]

AU - Kálmán, A.

AU - Argay, G.

AU - Sohár, P.

AU - Szabó, J.

AU - Fodor, L.

AU - Bernáth, G.

PY - 1986

Y1 - 1986

N2 - The stereochemistry of 2- and 4-phenyl-6,7-dimethoxy-3-methyl-3,4-dihydro-2H-1,3-benzothiazine (2,6) has been studied by 1H, 13C NMR spectroscopy and X-ray diffraction. Crystals of compound 2 (C17H19NO2S) are monoclinic, space group P21/n, with a = 11.428(1), b = 10.048(1), c = 14.161(2) Å, ß = 100.00(1)°, Z = 4, Dc = 1.247 g cm-3. Crystals of 6 are orthorhombic, space group P212121 with a = 7.068(1), b = 10.857(1), c = 20.343(1) Å, Z = 4, Dc = 1.247 g cm-3. The structures are refined to R = 0.041 for 2728 reflections of 2 and R = 0.039 for 1671 reflections of 6. The results unequivocally show that the 3-N-methyl group, and the 4-phenyl group are axial, while the 2-phenyl moiety is equatorial. Comparison are made between conformations of the title compounds and those of the following 1-phenyltetrahydroisoquinolines: unnatural cryptostyline II [2, 3], crypstostyline I [4] and 2-benzyl-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-phenyl-isoquinolinium iodide [5].

AB - The stereochemistry of 2- and 4-phenyl-6,7-dimethoxy-3-methyl-3,4-dihydro-2H-1,3-benzothiazine (2,6) has been studied by 1H, 13C NMR spectroscopy and X-ray diffraction. Crystals of compound 2 (C17H19NO2S) are monoclinic, space group P21/n, with a = 11.428(1), b = 10.048(1), c = 14.161(2) Å, ß = 100.00(1)°, Z = 4, Dc = 1.247 g cm-3. Crystals of 6 are orthorhombic, space group P212121 with a = 7.068(1), b = 10.857(1), c = 20.343(1) Å, Z = 4, Dc = 1.247 g cm-3. The structures are refined to R = 0.041 for 2728 reflections of 2 and R = 0.039 for 1671 reflections of 6. The results unequivocally show that the 3-N-methyl group, and the 4-phenyl group are axial, while the 2-phenyl moiety is equatorial. Comparison are made between conformations of the title compounds and those of the following 1-phenyltetrahydroisoquinolines: unnatural cryptostyline II [2, 3], crypstostyline I [4] and 2-benzyl-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-phenyl-isoquinolinium iodide [5].

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U2 - 10.1016/0022-2860(86)85038-4

DO - 10.1016/0022-2860(86)85038-4

M3 - Article

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VL - 145

SP - 341

EP - 354

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - 3-4

ER -