A multicomponent reaction between α-tetralone, 1H-tetrazol-5-amine, and aromatic aldehyde, occurring upon microwave irradiation in acidic medium at 130°C, led to the formation of previously unknown 7-aryl-5,6,7,12-tetrahydrobenzo[h]tetrazolo[5,1-b]quinazolines in 5–52% yields.
Similar content being viewed by others
References
Malinakova, H. C. Rep. Org. Chem. 2015, 5, 75.
Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.
Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323.
Biggs-Houck, J. E.; Younai, A.; Shaw, J. T. Curr. Opin. Chem. Biol. 2010, 14, 371.
Kappe, C. O. Tetrahedron 1993, 49, 6937.
Gore, R. P.; Rajput, A. P. Drug Invent. Today 2013, 5, 148.
Ryabukhin, S. V.; Plaskon, A. S.; Boron, S. Yu.; Volochnyuk, D. M.; Tolmachev, A. A. Mol. Diversity 2011, 15, 189.
Kidwai, M.; Chauhan, R. J. Mol. Catal. A: Chem. 2013, 377, 1.
Desenko, S. M.; Orlov, V. D.; Getmanskii, N. V.; Shishkin, O. V.; Lindeman, S. V.; Struchkov, Yu. T. Chem. Heterocycl. Compd. 1993, 29, 406. [Khim. Geterotsikl. Soedin. 1993, 481.]
Kolosov, M. A.; Shvets, E. H.; Kulyk, O. G.; Orlov, V. D. Chem. Heterocycl. Compd. 2015, 51, 1052. [Khim. Geterotsikl. Soedin. 2015, 51, 1052.]
Stadler, A.; Kappe, C. O. J. Chem. Soc., Perkin Trans. 2 2000, 1363.
Silverstein, R. M.; Webster F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds [Russian translation]; BINOM. Laboratoriya znanii: Moscow, 2011, p. 364.
Frumina, N. S.; Petrova, G. S.; Goryunova, N. N. In: Methods for Obtaining Chemical Reagents and Preparations [in Russian]; Lastovskii, R. P., Ed.; IREA: Moscow, 1967, Issue 15, p. 27.
This work was performed with financial support from the Russian Science Foundation (grant 14-50-00069).
The spectral data (NMR and high-resolution mass spectrometry) were obtained with the equipment at Saint Petersburg State University Research Park ''Research resources center for magnetic resonance'' and ''Center for chemical analysis and materials research''.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(11), 918–922
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(PDF 1802 kb)
Rights and permissions
About this article
Cite this article
Kantin, G.P., Krasavin, M. Reaction of α-tetralone, 1H-tetrazol-5-amine, and aromatic aldehydes upon microwave irradiation – a convenient method for the synthesis of 5,6,7,12-tetrahydrobenzo[h]tetrazolo[5,1-b]quinazolines. Chem Heterocycl Comp 52, 918–922 (2016). https://doi.org/10.1007/s10593-017-1985-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-017-1985-0