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.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.