Multicomponent Reaction Based Synthesis of 1-Tetrazolylimidazo[1,5- a]pyridines

Santosh Kurhade; Elmar Diekstra; Fandi Sutanto; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling

doi:10.1021/acs.orglett.8b01452

Multicomponent Reaction Based Synthesis of 1-Tetrazolylimidazo[1,5- a]pyridines

Santosh Kurhade, Elmar Diekstra, Fandi Sutanto, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Alexander Dömling

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Abstract

A series of unprecedented tetrazole-linked imidazo[1,5- a]pyridines are synthesized from simple and readily available building blocks. The reaction sequence involves an azido-Ugi-deprotection reaction followed by an acetic anhydride-mediated N-acylation-cyclization process to afford the target heterocycle. Furthermore, the scope of the methodology was extended to diverse R3-substitutions by employing commercial anhydrides, acid chlorides, and acids as an acyl component. The scope for the postmodification reactions are explored and the usefulness of the synthesis is exemplified by an improved three-step synthesis of a guanylate cyclase stimulator.

Original language	English
Pages (from-to)	3871-3874
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.8b01452
Publication status	Published - 6-Jul-2018

Keywords

acid anhydride
pyridine derivative
acylation
chemical structure
cyclization
synthesis

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10.1021/acs.orglett.8b01452Licence: CC BY-NC-ND

Multicomponent Reaction Based Synthesis of 1 ‑ Tetrazolylimidazo[1,5 ‑ a ]pyridinesFinal publisher's version, 1.49 MBLicence: CC BY-NC-ND

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CCDC 1839328: Experimental Crystal Structure Determination
Kurhade, S. (Contributor), Diekstra, E. (Contributor), Sutanto, F. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 24-Apr-2018
DOI: 10.5517/ccdc.csd.cc1zqz5v
Dataset
CCDC 1828260: Experimental Crystal Structure Determination
Kurhade, S. (Contributor), Diekstra, E. (Contributor), Sutanto, F. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 7-Mar-2018
DOI: 10.5517/ccdc.csd.cc1zcg4y
Dataset
CCDC 1828261: Experimental Crystal Structure Determination
Kurhade, S. (Contributor), Diekstra, E. (Contributor), Sutanto, F. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 7-Mar-2018
DOI: 10.5517/ccdc.csd.cc1zcg5z
Dataset

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title = "Multicomponent Reaction Based Synthesis of 1-Tetrazolylimidazo[1,5- a]pyridines",

abstract = "A series of unprecedented tetrazole-linked imidazo[1,5- a]pyridines are synthesized from simple and readily available building blocks. The reaction sequence involves an azido-Ugi-deprotection reaction followed by an acetic anhydride-mediated N-acylation-cyclization process to afford the target heterocycle. Furthermore, the scope of the methodology was extended to diverse R3-substitutions by employing commercial anhydrides, acid chlorides, and acids as an acyl component. The scope for the postmodification reactions are explored and the usefulness of the synthesis is exemplified by an improved three-step synthesis of a guanylate cyclase stimulator.",

keywords = "acid anhydride, pyridine derivative, acylation, chemical structure, cyclization, synthesis",

author = "Santosh Kurhade and Elmar Diekstra and Fandi Sutanto and Katarzyna Kurpiewska and Justyna Kalinowska-T{\l}u{\'s}cik and Alexander D{\"o}mling",

year = "2018",

month = jul,

day = "6",

doi = "10.1021/acs.orglett.8b01452",

language = "English",

volume = "20",

pages = "3871--3874",

journal = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

number = "13",

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TY - JOUR

T1 - Multicomponent Reaction Based Synthesis of 1-Tetrazolylimidazo[1,5- a]pyridines

AU - Kurhade, Santosh

AU - Diekstra, Elmar

AU - Sutanto, Fandi

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tłuścik, Justyna

AU - Dömling, Alexander

PY - 2018/7/6

Y1 - 2018/7/6

N2 - A series of unprecedented tetrazole-linked imidazo[1,5- a]pyridines are synthesized from simple and readily available building blocks. The reaction sequence involves an azido-Ugi-deprotection reaction followed by an acetic anhydride-mediated N-acylation-cyclization process to afford the target heterocycle. Furthermore, the scope of the methodology was extended to diverse R3-substitutions by employing commercial anhydrides, acid chlorides, and acids as an acyl component. The scope for the postmodification reactions are explored and the usefulness of the synthesis is exemplified by an improved three-step synthesis of a guanylate cyclase stimulator.

AB - A series of unprecedented tetrazole-linked imidazo[1,5- a]pyridines are synthesized from simple and readily available building blocks. The reaction sequence involves an azido-Ugi-deprotection reaction followed by an acetic anhydride-mediated N-acylation-cyclization process to afford the target heterocycle. Furthermore, the scope of the methodology was extended to diverse R3-substitutions by employing commercial anhydrides, acid chlorides, and acids as an acyl component. The scope for the postmodification reactions are explored and the usefulness of the synthesis is exemplified by an improved three-step synthesis of a guanylate cyclase stimulator.

KW - acid anhydride

KW - pyridine derivative

KW - acylation

KW - chemical structure

KW - cyclization

KW - synthesis

U2 - 10.1021/acs.orglett.8b01452

DO - 10.1021/acs.orglett.8b01452

M3 - Article

SN - 1523-7060

VL - 20

SP - 3871

EP - 3874

JO - Organic letters

JF - Organic letters

IS - 13

ER -

Multicomponent Reaction Based Synthesis of 1-Tetrazolylimidazo[1,5- a]pyridines

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Datasets

CCDC 1839328: Experimental Crystal Structure Determination

CCDC 1828260: Experimental Crystal Structure Determination

CCDC 1828261: Experimental Crystal Structure Determination

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