Synthesis of 6-(1H-Pyrrol-1-yl)azolo[1,5-a]pyrimidin-7-amines by the Clauson–Kaas Reaction
A series of pyrrolyl-substituted azolo[1,5-a]pyrimidine derivatives have been synthesized for the first time by the Clauson–Kaas reaction of the corresponding azolo[1,5-a]pyrimidine-6,7-diemines with 2,5-dimethoxytetrahydrofuran. The reaction has been found to selectively involve the amino group at the 6-position. The proposed approach makes it possible to obtain 6-(1H-pyrrol-1-yl)azolo[1,5-a]pyrimidin-7-amines in 64–85% yields with high purity. The product structure has been confirmed by NMR spectroscopy and X-ray analysis. The obtained results significantly extend the potential of modification of azolo[1,5-a]pyrimidines and open prospects for target-oriented synthesis of their functionalized derivatives.
Authors
- Павел А. Слепухин (ORCID: https://orcid.org/0000-0001-8132-9905)
- В. Л. Русинов (ORCID: https://orcid.org/0000-0002-1705-4078)
- Denis A. Gazizov (ORCID: https://orcid.org/0000-0003-4820-3205)
- Oleg S. Eltsov (ORCID: https://orcid.org/0000-0002-4681-2616)
- Semen V. Aminov (ORCID: https://orcid.org/0009-0000-8839-3491)
- Victor V. Fedotov (ORCID: https://orcid.org/0000-0002-4558-6848)
- Artyom O. Neymash
- E. N. Ulomskiy (ORCID: https://orcid.org/0000-0002-2957-1208)
- A. S. Kultyshev
Institutions
- Ural Federal University (RU)
- Institute of Organic Synthesis (RU)
- Ural Branch of the Russian Academy of Sciences (RU)
Publication Details
- Journal
- Russian Journal of Organic Chemistry
- Published
- 2025-04-01
- DOI
- https://doi.org/10.1134/s1070428025601062
- Primary Topic
- Synthesis and Reactions of Organic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00