Standard

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. / Presnukhina, Sofia ; Tarasenko, Marina; Baykov, Sergey; Smirnov, Sergey N.; Boyarskiy, Vadim P.; Shetnev, Anton; Korsakov, Mikhail K.

In: Tetrahedron Letters, Vol. 61, No. 9, 151543, 27.02.2020.

Research output: Contribution to journal › Article › peer-review

Harvard

Presnukhina, S, Tarasenko, M, Baykov, S, Smirnov, SN, Boyarskiy, VP, Shetnev, A & Korsakov, MK 2020, '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, 151543. https://doi.org/10.1016/j.tetlet.2019.151543

APA

Presnukhina, S., Tarasenko, M., Baykov, S., Smirnov, S. N., Boyarskiy, V. P., Shetnev, A., & Korsakov, M. K. (2020). 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, 61(9), [151543]. https://doi.org/10.1016/j.tetlet.2019.151543

Vancouver

Presnukhina S, Tarasenko M, Baykov S, Smirnov SN, Boyarskiy VP, Shetnev A 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 Feb 27;61(9). 151543. https://doi.org/10.1016/j.tetlet.2019.151543

Author

Presnukhina, Sofia ; Tarasenko, Marina ; Baykov, Sergey ; Smirnov, Sergey N. ; Boyarskiy, Vadim P. ; Shetnev, Anton ; Korsakov, Mikhail 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. In: Tetrahedron Letters. 2020 ; Vol. 61, No. 9.

BibTeX

@article{147de603beeb495bb45e534ae37404b3,
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",
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).",
keywords = "Acrylic acids, Dicarboxylic acid anhydrides, Heterocycles, Retro-Diels-Alder reaction, CANCER-CELLS, HISTONE DEACETYLASE INHIBITOR, NUCLEAR EXPORT, SELINEXOR, DISCOVERY, SELECTIVE INHIBITOR, BIOLOGICAL EVALUATION, DIFFERENTIATION, PHASE-I, DERIVATIVES",
author = "Sofia Presnukhina and Marina Tarasenko and Sergey Baykov and Smirnov, {Sergey N.} and Boyarskiy, {Vadim P.} and Anton Shetnev and Korsakov, {Mikhail K.}",
year = "2020",
month = feb,
day = "27",
doi = "10.1016/j.tetlet.2019.151543",
language = "English",
volume = "61",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "9",

}

RIS

TY - JOUR

T1 - 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

AU - Presnukhina, Sofia

AU - Tarasenko, Marina

AU - Baykov, Sergey

AU - Smirnov, Sergey N.

AU - Boyarskiy, Vadim P.

AU - Shetnev, Anton

AU - Korsakov, Mikhail K.

PY - 2020/2/27

Y1 - 2020/2/27

N2 - 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).

AB - 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).

KW - Acrylic acids

KW - Dicarboxylic acid anhydrides

KW - Heterocycles

KW - Retro-Diels-Alder reaction

KW - CANCER-CELLS

KW - HISTONE DEACETYLASE INHIBITOR

KW - NUCLEAR EXPORT

KW - SELINEXOR

KW - DISCOVERY

KW - SELECTIVE INHIBITOR

KW - BIOLOGICAL EVALUATION

KW - DIFFERENTIATION

KW - PHASE-I

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85076836187&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/87727fa8-636c-30b2-9b22-00314d9dbe05/

U2 - 10.1016/j.tetlet.2019.151543

DO - 10.1016/j.tetlet.2019.151543

M3 - Article

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 9

M1 - 151543

ER -

ID: 51875841