Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile

Anton A. Muravev; Svetlana E. Solovieva; Farida B. Galieva; Olga B. Bazanova; Ildar Kh. Rizvanov; Kamil A. Ivshin; Olga N. Kataeva; Susan E. Matthews; Igor S. Antipin

doi:10.1039/C8RA06349D

Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile

Anton A. Muravev, Svetlana E. Solovieva, Farida B. Galieva, Olga B. Bazanova, Ildar Kh. Rizvanov, Kamil A. Ivshin, Olga N. Kataeva, Susan E. Matthews, Igor S. Antipin

School of Natural Sciences

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

5 Citations (Scopus)

19 Downloads (Pure)

Abstract

Late stage diversification of calix[4]arenes and thiacalix[4]arenes with heterocycles remains a significant synthetic challenge and hampers further exploitation of the scaffolds. Here we describe the development of a short and facile synthetic route to conformationally diverse novel calix[4]arene and thiacalix[4]arene ynones using a palladium cross coupling approach (5% Pd(II) + 10% Cu(I)) with benzoyl chloride. Their successful conversion to heterocycles to afford pyrazoles was demonstrated through treatment with hydrazine. Functionalisation is calixarene conformation and linker independent enabling access to a library of structures.

Original language	English
Pages (from-to)	32765-32769
Journal	RSC Advances
Volume	8
Issue number	57
DOIs	https://doi.org/10.1039/C8RA06349D
Publication status	Published - 21 Sep 2018

Access to Document

10.1039/C8RA06349DLicence: CC BY-NC

Published manuscript
This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
Final published version, 620 KBLicence: CC BY-NC

http://xlink.rsc.org/?DOI=C8RA06349DLicence: CC BY-NC

Cite this

@article{72eb0a600a284cd0a97ce6ff2ea2c80b,

title = "Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile",

abstract = "Late stage diversification of calix[4]arenes and thiacalix[4]arenes with heterocycles remains a significant synthetic challenge and hampers further exploitation of the scaffolds. Here we describe the development of a short and facile synthetic route to conformationally diverse novel calix[4]arene and thiacalix[4]arene ynones using a palladium cross coupling approach (5% Pd(II) + 10% Cu(I)) with benzoyl chloride. Their successful conversion to heterocycles to afford pyrazoles was demonstrated through treatment with hydrazine. Functionalisation is calixarene conformation and linker independent enabling access to a library of structures.",

author = "Muravev, {Anton A.} and Solovieva, {Svetlana E.} and Galieva, {Farida B.} and Bazanova, {Olga B.} and Rizvanov, {Ildar Kh.} and Ivshin, {Kamil A.} and Olga N. Kataeva and Matthews, {Susan E.} and Antipin, {Igor S.}",

year = "2018",

month = sep,

day = "21",

doi = "10.1039/C8RA06349D",

language = "English",

volume = "8",

pages = "32765--32769",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "57",

}

Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile. / Muravev, Anton A.; Solovieva, Svetlana E.; Galieva, Farida B.; Bazanova, Olga B.; Rizvanov, Ildar Kh.; Ivshin, Kamil A.; Kataeva, Olga N.; Matthews, Susan E.; Antipin, Igor S.

In: RSC Advances, Vol. 8, No. 57, 21.09.2018, p. 32765-32769.

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

TY - JOUR

T1 - Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile

AU - Muravev, Anton A.

AU - Solovieva, Svetlana E.

AU - Galieva, Farida B.

AU - Bazanova, Olga B.

AU - Rizvanov, Ildar Kh.

AU - Ivshin, Kamil A.

AU - Kataeva, Olga N.

AU - Matthews, Susan E.

AU - Antipin, Igor S.

PY - 2018/9/21

Y1 - 2018/9/21

N2 - Late stage diversification of calix[4]arenes and thiacalix[4]arenes with heterocycles remains a significant synthetic challenge and hampers further exploitation of the scaffolds. Here we describe the development of a short and facile synthetic route to conformationally diverse novel calix[4]arene and thiacalix[4]arene ynones using a palladium cross coupling approach (5% Pd(II) + 10% Cu(I)) with benzoyl chloride. Their successful conversion to heterocycles to afford pyrazoles was demonstrated through treatment with hydrazine. Functionalisation is calixarene conformation and linker independent enabling access to a library of structures.

AB - Late stage diversification of calix[4]arenes and thiacalix[4]arenes with heterocycles remains a significant synthetic challenge and hampers further exploitation of the scaffolds. Here we describe the development of a short and facile synthetic route to conformationally diverse novel calix[4]arene and thiacalix[4]arene ynones using a palladium cross coupling approach (5% Pd(II) + 10% Cu(I)) with benzoyl chloride. Their successful conversion to heterocycles to afford pyrazoles was demonstrated through treatment with hydrazine. Functionalisation is calixarene conformation and linker independent enabling access to a library of structures.

U2 - 10.1039/C8RA06349D

DO - 10.1039/C8RA06349D

M3 - Article

VL - 8

SP - 32765

EP - 32769

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 57

ER -