Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence
Vladislava V Matveevskaya
1
,
Marina Tarasenko
2
,
Sergey N Smirnov
3
,
Anton A Shetnev
1
,
Mikhail K Korsakov
1
Publication type: Journal Article
Publication date: 2020-02-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A simple and convenient one-pot method is reported for the synthesis of (E)-3-(3-aryl(heteroaryl, alkyl)-1,2,4-oxadiazole-5-yl)acrylic acids utilizing readily accessible or commercially available substituted benzamidoximes and inexpensive exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. The method is based on the reaction of amidoximes with the anhydride in a basic medium at RT followed by an acid-catalyzed retro-Diels-Alder reaction. The observed stereoselective heterocyclization/retro-Diels-Alder cascade process is suitable for the synthesis of a wide range of substituted (E)-1,2,4-oxadiazole-5-ylacrylic acids featuring electron donating and electron withdrawing groups on the aryl moiety, as well as heteroaryl or alkyl substituents at position 3 of the 1,2,4-oxadiazole ring (42–79%; 15 examples).
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Total citations:
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Citations from 2024:
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(30.77%)
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GOST
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Presnukhina S. I. et al. Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence // Tetrahedron Letters. 2020. Vol. 61. No. 9. p. 151543.
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Presnukhina S. I., Matveevskaya V. V., Tarasenko M., Smirnov S. N., Boyarskiy V. P., Shetnev A. A., Korsakov M. K. Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence // Tetrahedron Letters. 2020. Vol. 61. No. 9. p. 151543.
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RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2019.151543
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040403919313425
TI - Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence
T2 - Tetrahedron Letters
AU - Presnukhina, Sofia I
AU - Matveevskaya, Vladislava V
AU - Tarasenko, Marina
AU - Smirnov, Sergey N
AU - Boyarskiy, Vadim P
AU - Shetnev, Anton A
AU - Korsakov, Mikhail K
PY - 2020
DA - 2020/02/01
PB - Elsevier
SP - 151543
IS - 9
VL - 61
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Presnukhina,
author = {Sofia I Presnukhina and Vladislava V Matveevskaya and Marina Tarasenko and Sergey N Smirnov and Vadim P Boyarskiy and Anton A Shetnev and Mikhail K Korsakov},
title = {Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence},
journal = {Tetrahedron Letters},
year = {2020},
volume = {61},
publisher = {Elsevier},
month = {feb},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0040403919313425},
number = {9},
pages = {151543},
doi = {10.1016/j.tetlet.2019.151543}
}
Cite this
MLA
Copy
Presnukhina, Sofia I., et al. “Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence.” Tetrahedron Letters, vol. 61, no. 9, Feb. 2020, p. 151543. https://linkinghub.elsevier.com/retrieve/pii/S0040403919313425.