Two-step synthesis of monoterpenoid dioxinols exhibiting analgesic activity from isopulegol and benzaldehyde over heterogeneous catalysts

Martina Stekrova; Päivi Mäki-Arvela; Ewelina Leino; Karolina Maduna Valkaj; Kari Eränen; Atte Aho; Annika Smeds; Narendra Kumar; Konstantin P. Volcho; Nariman F. Salakhutdinov; Dmitry Murzin

doi:10.1016/j.cattod.2016.03.046

Two-step synthesis of monoterpenoid dioxinols exhibiting analgesic activity from isopulegol and benzaldehyde over heterogeneous catalysts

Martina Stekrova, Päivi Mäki-Arvela, Ewelina Leino, Karolina Maduna Valkaj, Kari Eränen, Atte Aho, Annika Smeds, Narendra Kumar, Konstantin P. Volcho, Nariman F. Salakhutdinov, Dmitry Murzin

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

6 Citations (Scopus)

Abstract

Benzodioxinols, compounds with 6-membered heterocycles containing two oxygen atoms, exhibit promising analgesic activity. In the current study, synthesis of dioxinol via two-step approach including Prins cyclization of isopulegol with benzaldehyde to tetrahydropyran and its ring-rearrangement to dioxinol was investigated. Different acidic and basic catalysts were studied in the second step and the highest selectivity toward dioxinol was achieved using mesoporous Ce-composite material.

Original language	Undefined/Unknown
Pages (from-to)	56–62
Journal	Catalysis Today
Volume	279, Part 1
DOIs	https://doi.org/10.1016/j.cattod.2016.03.046
Publication status	Published - 2017
MoE publication type	A1 Journal article-refereed

Keywords

engineering education

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10.1016/j.cattod.2016.03.046

http://www.sciencedirect.com/science/article/pii/S0920586116302279

Cite this

Stekrova, M., Mäki-Arvela, P., Leino, E., Maduna Valkaj, K., Eränen, K., Aho, A., Smeds, A., Kumar, N., Volcho, K. P., Salakhutdinov, N. F., & Murzin, D. (2017). Two-step synthesis of monoterpenoid dioxinols exhibiting analgesic activity from isopulegol and benzaldehyde over heterogeneous catalysts. Catalysis Today, 279, Part 1, 56–62. https://doi.org/10.1016/j.cattod.2016.03.046

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title = "Two-step synthesis of monoterpenoid dioxinols exhibiting analgesic activity from isopulegol and benzaldehyde over heterogeneous catalysts",

abstract = "Benzodioxinols, compounds with 6-membered heterocycles containing two oxygen atoms, exhibit promising analgesic activity. In the current study, synthesis of dioxinol via two-step approach including Prins cyclization of isopulegol with benzaldehyde to tetrahydropyran and its ring-rearrangement to dioxinol was investigated. Different acidic and basic catalysts were studied in the second step and the highest selectivity toward dioxinol was achieved using mesoporous Ce-composite material.",

keywords = "engineering education, engineering education, engineering education",

author = "Martina Stekrova and P{\"a}ivi M{\"a}ki-Arvela and Ewelina Leino and {Maduna Valkaj}, Karolina and Kari Er{\"a}nen and Atte Aho and Annika Smeds and Narendra Kumar and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.} and Dmitry Murzin",

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Stekrova, M, Mäki-Arvela, P, Leino, E, Maduna Valkaj, K, Eränen, K , Aho, A, Smeds, A, Kumar, N, Volcho, KP, Salakhutdinov, NF & Murzin, D 2017, 'Two-step synthesis of monoterpenoid dioxinols exhibiting analgesic activity from isopulegol and benzaldehyde over heterogeneous catalysts', Catalysis Today, vol. 279, Part 1, pp. 56–62. https://doi.org/10.1016/j.cattod.2016.03.046

TY - JOUR

T1 - Two-step synthesis of monoterpenoid dioxinols exhibiting analgesic activity from isopulegol and benzaldehyde over heterogeneous catalysts

AU - Stekrova, Martina

AU - Mäki-Arvela, Päivi

AU - Leino, Ewelina

AU - Maduna Valkaj, Karolina

AU - Eränen, Kari

AU - Aho, Atte

AU - Smeds, Annika

AU - Kumar, Narendra

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

AU - Murzin, Dmitry

N1 - tk. 3pk EuropaCat XII: Catalysis for Chemical Synthesis

PY - 2017

Y1 - 2017

N2 - Benzodioxinols, compounds with 6-membered heterocycles containing two oxygen atoms, exhibit promising analgesic activity. In the current study, synthesis of dioxinol via two-step approach including Prins cyclization of isopulegol with benzaldehyde to tetrahydropyran and its ring-rearrangement to dioxinol was investigated. Different acidic and basic catalysts were studied in the second step and the highest selectivity toward dioxinol was achieved using mesoporous Ce-composite material.

AB - Benzodioxinols, compounds with 6-membered heterocycles containing two oxygen atoms, exhibit promising analgesic activity. In the current study, synthesis of dioxinol via two-step approach including Prins cyclization of isopulegol with benzaldehyde to tetrahydropyran and its ring-rearrangement to dioxinol was investigated. Different acidic and basic catalysts were studied in the second step and the highest selectivity toward dioxinol was achieved using mesoporous Ce-composite material.

KW - engineering education

U2 - 10.1016/j.cattod.2016.03.046

DO - 10.1016/j.cattod.2016.03.046

M3 - Artikel

SN - 0920-5861

VL - 279, Part 1

SP - 56

EP - 62

JO - Catalysis Today

JF - Catalysis Today

ER -