Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-alpha]pyridin-1-yl)-1,3,4-Oxadiazoles

Santosh Kurhade; Markella Konstantinidou; Fandi Sutanto; Katarzyna Kurpiewska; Justyna Kalinowska-Tluscik; Alexander Domling

doi:10.1002/ejoc.201801880

Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-alpha]pyridin-1-yl)-1,3,4-Oxadiazoles

Santosh Kurhade
, Markella Konstantinidou
, Fandi Sutanto
, Katarzyna Kurpiewska
, Justyna Kalinowska-Tluscik
, Alexander Domling^*

^*Corresponding author for this work

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Abstract

A 21 membered library of 2-(imidazo[1,5-alpha]pyridine-1-yl)-1,3,4-oxadiazoles is synthesized in an unprecedented short sequence starting from an Ugi tetrazole reaction with a cleavable isocyanide component. The intermediate tetrazole is subjected to an acetic anhydride-mediated cyclization, followed by a Huisgen-type rearrangement with acyl chlorides to afford the imidazopyridine-oxadiazole bis-heterocycles. The scope and limitations of the methodology were investigated with substitutions on both the oxadiazole and the imidazopyridine rings. The introduced enabling technology for imidazopyridine oxadiazole synthesis combines a short reaction sequence with high scaffold diversity, based on commercially available starting materials and high functional groups tolerance.

Original language	English
Pages (from-to)	2029-2034
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	10
DOIs	https://doi.org/10.1002/ejoc.201801880
Publication status	Published - 14-Mar-2019

Keywords

MCR chemistry
Oxadiazoles
Huisgen rearrangement
Tetrazoles
Imidazopyridines
SPECTRAL-LUMINESCENT PROPERTIES
1,3,4-OXADIAZOLE DERIVATIVES
TETRAZOLES
ACYLATION

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10.1002/ejoc.201801880

Manuscript-Sequential Multicomponent Synthesis of 2‐(Imidazo[1,5‐α]pyridin‐1‐yl)‐1,3,4‐OxadiazolesSubmitted manuscript, 740 KB
Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-α]-pyridin-1-yl)-1,3,4-OxadiazolesFinal publisher's version, 1.13 MBLicence: Taverne

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CCDC 1869773: Experimental Crystal Structure Determination
Kurhade, S. (Contributor), Konstantinidou, M. (Contributor), Sutanto, F. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 25-Sept-2018
DOI: 10.5517/ccdc.csd.cc20rn8q
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@article{a0829c60901e42d5a0be6f717dd5867b,

title = "Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-alpha]pyridin-1-yl)-1,3,4-Oxadiazoles",

abstract = "A 21 membered library of 2-(imidazo[1,5-alpha]pyridine-1-yl)-1,3,4-oxadiazoles is synthesized in an unprecedented short sequence starting from an Ugi tetrazole reaction with a cleavable isocyanide component. The intermediate tetrazole is subjected to an acetic anhydride-mediated cyclization, followed by a Huisgen-type rearrangement with acyl chlorides to afford the imidazopyridine-oxadiazole bis-heterocycles. The scope and limitations of the methodology were investigated with substitutions on both the oxadiazole and the imidazopyridine rings. The introduced enabling technology for imidazopyridine oxadiazole synthesis combines a short reaction sequence with high scaffold diversity, based on commercially available starting materials and high functional groups tolerance.",

keywords = "MCR chemistry, Oxadiazoles, Huisgen rearrangement, Tetrazoles, Imidazopyridines, SPECTRAL-LUMINESCENT PROPERTIES, 1,3,4-OXADIAZOLE DERIVATIVES, TETRAZOLES, ACYLATION",

author = "Santosh Kurhade and Markella Konstantinidou and Fandi Sutanto and Katarzyna Kurpiewska and Justyna Kalinowska-Tluscik and Alexander Domling",

year = "2019",

month = mar,

day = "14",

doi = "10.1002/ejoc.201801880",

language = "English",

volume = "2019",

pages = "2029--2034",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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number = "10",

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TY - JOUR

T1 - Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-alpha]pyridin-1-yl)-1,3,4-Oxadiazoles

AU - Kurhade, Santosh

AU - Konstantinidou, Markella

AU - Sutanto, Fandi

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tluscik, Justyna

AU - Domling, Alexander

PY - 2019/3/14

Y1 - 2019/3/14

N2 - A 21 membered library of 2-(imidazo[1,5-alpha]pyridine-1-yl)-1,3,4-oxadiazoles is synthesized in an unprecedented short sequence starting from an Ugi tetrazole reaction with a cleavable isocyanide component. The intermediate tetrazole is subjected to an acetic anhydride-mediated cyclization, followed by a Huisgen-type rearrangement with acyl chlorides to afford the imidazopyridine-oxadiazole bis-heterocycles. The scope and limitations of the methodology were investigated with substitutions on both the oxadiazole and the imidazopyridine rings. The introduced enabling technology for imidazopyridine oxadiazole synthesis combines a short reaction sequence with high scaffold diversity, based on commercially available starting materials and high functional groups tolerance.

AB - A 21 membered library of 2-(imidazo[1,5-alpha]pyridine-1-yl)-1,3,4-oxadiazoles is synthesized in an unprecedented short sequence starting from an Ugi tetrazole reaction with a cleavable isocyanide component. The intermediate tetrazole is subjected to an acetic anhydride-mediated cyclization, followed by a Huisgen-type rearrangement with acyl chlorides to afford the imidazopyridine-oxadiazole bis-heterocycles. The scope and limitations of the methodology were investigated with substitutions on both the oxadiazole and the imidazopyridine rings. The introduced enabling technology for imidazopyridine oxadiazole synthesis combines a short reaction sequence with high scaffold diversity, based on commercially available starting materials and high functional groups tolerance.

KW - MCR chemistry

KW - Oxadiazoles

KW - Huisgen rearrangement

KW - Tetrazoles

KW - Imidazopyridines

KW - SPECTRAL-LUMINESCENT PROPERTIES

KW - 1,3,4-OXADIAZOLE DERIVATIVES

KW - TETRAZOLES

KW - ACYLATION

U2 - 10.1002/ejoc.201801880

DO - 10.1002/ejoc.201801880

M3 - Article

SN - 1434-193X

VL - 2019

SP - 2029

EP - 2034

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 10

ER -

Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-alpha]pyridin-1-yl)-1,3,4-Oxadiazoles

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CCDC 1869773: Experimental Crystal Structure Determination

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