Unusual in Water Multicomponent Reaction of 3-Amino-5-methylpyrazole, Acetylacetone and Aldehyde

Irina Tkachenko, Sergey Komykhov, Vladimir Musatov, Valentyn Chebanov, Sergey Desenko


Multicomponent reaction of 3-amino-5-methylpyrazole, aliphatic aldehyde (paraformaldehyde or acetaldehyde) and acetylacetone in water by conventional heating, microwave or ultrasound activation undergoes on molar amounts of reagents 2:1:2, respectively, leads bis(2,5,7-trimethylpyrazolo[1,5-a]pyrimidin-6-yl)-substituted methane or to corresponding 1,1-bis-substituted ethane.


multicomponent reactions; heterocycles; 3-aminopyrazole derivative; in water synthesis; microwave-assisted synthesis; ultrasonication

Full Text:



Zhu J, Bienayme H. Multicomponent Reactions. Wiley-VCH: 2005; 484 p. https://doi.org/10.1002/3527605118

Wermann K, Hartmann M. Synthesis of Dihydro-1,2,4-triazolo[1,5-a]pyrimidines. Synthesis 1991;1991(03):189-191. https://doi.org/10.1055/s-1991-26414

Chebanov VA, Desenko SM, Gurley TW, Azaheterocycles Based on α, β-Unsaturated Carbonyls. Springer; 2008, 212 p. https://doi.org/10.1007/978-3-540-68367-4

Rudenko R, Komykhov S, Musatov V, Desenko S. New dihydro-1,2,4-triazolo[1,5-a]pyrimidines based on arylidene derivatives of 5-acetylbarbituric and dehydroacetic acids. Journal of Heterocyclic Chemistry 2009;46(2):285-288. https://doi.org/10.1002/jhet.81

Kolosov M, Beloborodov D, Orlov V, Dotsenko V. Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-a]pyrimidines. New Journal of Chemistry 2016;40(9):7573-7579. https://doi.org/10.1039/c6nj00336b

Kour P, Singh V, Khajuria B, Singh T, Kumar A. Al(III) chloride catalyzed multi-component domino strategy: Synthesis of library of dihydrotetrazolo[1,5- a ]pyrimidines and tetrahydrotetrazolo[1,5- a ]quinazolinones. Tetrahedron Letters 2017;58(44):4179-4185. https://doi.org/10.1016/j.tetlet.2017.09.052

Lancaster M. Green Chemistry: An Introductory Text. Cambridge: RSC; 2002, p 5. https://doi.org/10.1039/9781847551009-fx001

Grieco PA. Organic Synthesis in Water. Springer; 1998, p 302. https://doi.org/10.1007/978-94-011-4950-1

Komykhov SA, Tkachenko IG, Musatov VI, Diachkov MV, Chebanov VA, Desenko SM. Multicomponent synthesis in water of 7-unsubstituted 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines and their antimicrobial and antifungal activity. Arkivoc 2016; (iv): 277-287. https://doi.org/10.3998/ark.5550190.p009.610

Tkachenko I, Komykhov S, Gladkov E, Musatov V, Chebanov V, Desenko S. Acetic aldehyde in multicomponent synthesis of azolopyrimidine derivatives in water. Chemistry of Heterocyclic Compounds 2019;55(4-5):392-396. https://doi.org/10.1007/s10593-019-02470-0

Leeson P. Chemical beauty contest. Nature 2012;481(7382):455-456. https://doi.org/10.1038/481455a