New synthesis of steroidal tetrahydrooxazin-2-ones 1 1 Preliminary communication

Gy. Schneider, L. Hackler and Gy. Dombi, J. Chem. Soc. Chem. Comm., 1980, 891.

G. Schneider, László Hackler, P. Sohár

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Abstract

In the DMSO/NaHCO3 system, 16α-aminomethyl-, 16α-benzylaminomethyl- and substituted benzylaminomethyl-3-methoxy-17β-tosyloxyestra-1,3, 5(10)-triene (3, 5a-k) do not undergo oxidation, but form a tetrahydrooxa-zin-2-one ring (7, 8a-k) via neighboring group participation. Under similar conditions, 16β-aminomethyl-3-methoxy-17β-tosylestra-1,3,5(10)-triene (4) decomposes into 16-methylene-3-methoxyestra-l,3,5(10)-trien-17-one (12).

Original languageEnglish
Pages (from-to)3987-3995
Number of pages9
JournalTetrahedron
Volume43
Issue number17
DOIs
Publication statusPublished - 1987

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Trientine
Dimethyl Sulfoxide
Oxidation
Communication

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{b1651eb69ef146a09261d9bf22d4b548,
title = "New synthesis of steroidal tetrahydrooxazin-2-ones 1 1 Preliminary communication: Gy. Schneider, L. Hackler and Gy. Dombi, J. Chem. Soc. Chem. Comm., 1980, 891.",
abstract = "In the DMSO/NaHCO3 system, 16α-aminomethyl-, 16α-benzylaminomethyl- and substituted benzylaminomethyl-3-methoxy-17β-tosyloxyestra-1,3, 5(10)-triene (3, 5a-k) do not undergo oxidation, but form a tetrahydrooxa-zin-2-one ring (7, 8a-k) via neighboring group participation. Under similar conditions, 16β-aminomethyl-3-methoxy-17β-tosylestra-1,3,5(10)-triene (4) decomposes into 16-methylene-3-methoxyestra-l,3,5(10)-trien-17-one (12).",
author = "G. Schneider and L{\'a}szl{\'o} Hackler and P. Soh{\'a}r",
year = "1987",
doi = "10.1016/S0040-4020(01)81681-1",
language = "English",
volume = "43",
pages = "3987--3995",
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issn = "0040-4020",
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T1 - New synthesis of steroidal tetrahydrooxazin-2-ones 1 1 Preliminary communication

T2 - Gy. Schneider, L. Hackler and Gy. Dombi, J. Chem. Soc. Chem. Comm., 1980, 891.

AU - Schneider, G.

AU - Hackler, László

AU - Sohár, P.

PY - 1987

Y1 - 1987

N2 - In the DMSO/NaHCO3 system, 16α-aminomethyl-, 16α-benzylaminomethyl- and substituted benzylaminomethyl-3-methoxy-17β-tosyloxyestra-1,3, 5(10)-triene (3, 5a-k) do not undergo oxidation, but form a tetrahydrooxa-zin-2-one ring (7, 8a-k) via neighboring group participation. Under similar conditions, 16β-aminomethyl-3-methoxy-17β-tosylestra-1,3,5(10)-triene (4) decomposes into 16-methylene-3-methoxyestra-l,3,5(10)-trien-17-one (12).

AB - In the DMSO/NaHCO3 system, 16α-aminomethyl-, 16α-benzylaminomethyl- and substituted benzylaminomethyl-3-methoxy-17β-tosyloxyestra-1,3, 5(10)-triene (3, 5a-k) do not undergo oxidation, but form a tetrahydrooxa-zin-2-one ring (7, 8a-k) via neighboring group participation. Under similar conditions, 16β-aminomethyl-3-methoxy-17β-tosylestra-1,3,5(10)-triene (4) decomposes into 16-methylene-3-methoxyestra-l,3,5(10)-trien-17-one (12).

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JF - Tetrahedron

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