Synthesis of (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione: a potential synthon for the preparation of novel heteroaryl-annulated bicyclic morpholines
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Pfizer Worldwide Research and Development, Eastern Point Rd, Groton, CT, 06340, USA
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Publication type: Journal Article
Publication date: 2011-09-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The novel bridged bicyclic morpholinethione (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione (9) has been prepared in six steps. This conformationally restricted morpholinethione was prepared stereoselectively using straightforward chemistry and inexpensive starting materials. The key oxetane ring was formed via an intramolecular alkylation reaction.
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Wishka D. G., Walker D. Synthesis of (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione: a potential synthon for the preparation of novel heteroaryl-annulated bicyclic morpholines // Tetrahedron Letters. 2011. Vol. 52. No. 37. pp. 4713-4715.
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Wishka D. G., Walker D. Synthesis of (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione: a potential synthon for the preparation of novel heteroaryl-annulated bicyclic morpholines // Tetrahedron Letters. 2011. Vol. 52. No. 37. pp. 4713-4715.
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TY - JOUR
DO - 10.1016/j.tetlet.2011.07.017
UR - https://doi.org/10.1016/j.tetlet.2011.07.017
TI - Synthesis of (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione: a potential synthon for the preparation of novel heteroaryl-annulated bicyclic morpholines
T2 - Tetrahedron Letters
AU - Wishka, Donn G.
AU - Walker, Daniel
PY - 2011
DA - 2011/09/01
PB - Elsevier
SP - 4713-4715
IS - 37
VL - 52
SN - 0040-4039
SN - 1873-3581
ER -
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@article{2011_Wishka,
author = {Donn G. Wishka and Daniel Walker},
title = {Synthesis of (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione: a potential synthon for the preparation of novel heteroaryl-annulated bicyclic morpholines},
journal = {Tetrahedron Letters},
year = {2011},
volume = {52},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.tetlet.2011.07.017},
number = {37},
pages = {4713--4715},
doi = {10.1016/j.tetlet.2011.07.017}
}
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Wishka, Donn G., and Daniel Walker. “Synthesis of (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione: a potential synthon for the preparation of novel heteroaryl-annulated bicyclic morpholines.” Tetrahedron Letters, vol. 52, no. 37, Sep. 2011, pp. 4713-4715. https://doi.org/10.1016/j.tetlet.2011.07.017.