Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 4
217
Views
4
CrossRef citations to date
0
Altmetric
Articles

A synthesis of 6-functionalized 7-unsubstituted- and 7-methyl[1,2,4]azolo[1,5-a]pyrimidine derivatives

ORCID Icon, ORCID Icon, , , & ORCID Icon
Pages 611-615 | Received 03 Nov 2018, Accepted 03 Jan 2019, Published online: 29 Jan 2019
 

Abstract

6-Functionalized 7-R-4,7-dihydro[1,2,4]azolo[1,5-a]pyrimidines (R = H or Me) were synthesized by Biginelli-like reaction of formaldehyde or acetaldehyde, aminoazoles, and corresponding β-dicarbonyl precursor. Alkylation of the obtained compounds proceeds smoothly at position 4, while oxidation leads to 7-R-[1,2,4]azolo[1,5-a]pyrimidines formation. 6-Ethoxycarbonyl derivatives could be reduced to the corresponding alcohols by LiAlH4 and hydrolyzed to the acids.

GRAPHICAL ABSTRACT

Acknowledgments

We thank V. I. Musatov, V. V. Vashchenko, E. V. Vashchenko (STC “Institute for Single Crystals” NAS of Ukraine) and Enamine Ltd. for spectroscopic measurements and A. Yu. Lyapunov (A. V. Bogatsky Physico-Chemical Institute NAS of Ukraine) for fruitful discussion.

Additional information

Funding

This work was supported by V. N. Karazin Kharkiv National University under Grant 811н/12-17.

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 422.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.