Journal of Flow Chemistry
Volume/Issue:
Volume 4: Issue 3
A Facile Route to Triazolopyrimidines Using a [3+2] Cycloaddition and Continuous-Flow Chemistry
Authors:
Sara Sadler Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Meaghan M. Sebeika Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Nicholas L. Kern Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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David E. Bell Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Chloe A. Laverack Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Devan J. Wilkins Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Alexander R. Moeller Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Benjamin C. Nicolaysen Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Paige N. Kozlowski Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Charlotte Wiles Chemtrix BV, Chemelot Campus, Urmonderbaan, 22, 6167, RD, Geleen, The Netherlands

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Robert J. Tinder Proteaf Technologies, LLC, 904 Silver Spur Rd. #481, Palos Verdes, Estates, CA, 90274, USA

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Graham B. Jones Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

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Pages:
140–147
Online Publication Date:
17 Sep 2014
Publication Date:
17 Sep 2014
Article Category:
Research Article
DOI:
https://doi.org/10.1556/jfc-d-14-00019
Keywords:
[3+2] cycloaddition; azide; continuous flow; triazole; triazolopyrimidine; one-pot reaction
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Abstract

A facile and benign route to N-heterocycles, including triazoles and triazolopyrimidines, has been developed. Using continuous-flow microreactor technology, organic azides are prepared in situ and reacted with cyanoacetamide in a [3+2] cycloaddition to produce a variety of substituted 1,2,3-triazoles, which can be elaborated into useful building blocks. A benzyl-substituted triazole was further functionalized to an analog of the core structure of the antiplatelet agent Brilinta®. The methodology lends itself well to flow chemistry, where reaction volumes are minimized, heating and mixing are consistent, and the need for intermediate azide isolation bypassed. The scope of the process is wide, and the efficiency is high, suggesting this as a practical, green route for the production of triazolo-based heterocycles.

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Cover Journal of Flow Chemistry
Journal of Flow Chemistry A Journal of the Flow Chemistry Society
Print ISSN:
2062-249X
Online ISSN:
2063-0212

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Journal of Flow Chemistry
Language English
Size A4
Year of
Foundation		 2011
Volumes
per Year		 1
Issues
per Year		 4
Founder Áramlásos Kémiai Tudományos Társaság
Founder's
Address		 H-1031 Budapest, Hungary Záhony utca 7.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible
Publisher		 Chief Executive Officer, Akadémiai Kiadó
ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)

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