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

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.

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  1. 1.

    Malinakova, H. C. Rep. Org. Chem. 2015, 5, 75.

    CAS  Article  Google Scholar 

  2. 2.

    Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.

    Article  Google Scholar 

  3. 3.

    Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323.

    CAS  Article  Google Scholar 

  4. 4.

    Biggs-Houck, J. E.; Younai, A.; Shaw, J. T. Curr. Opin. Chem. Biol. 2010, 14, 371.

    CAS  Article  Google Scholar 

  5. 5.

    Kappe, C. O. Tetrahedron 1993, 49, 6937.

    CAS  Article  Google Scholar 

  6. 6.

    Gore, R. P.; Rajput, A. P. Drug Invent. Today 2013, 5, 148.

    CAS  Article  Google Scholar 

  7. 7.

    Ryabukhin, S. V.; Plaskon, A. S.; Boron, S. Yu.; Volochnyuk, D. M.; Tolmachev, A. A. Mol. Diversity 2011, 15, 189.

    CAS  Article  Google Scholar 

  8. 8.

    Kidwai, M.; Chauhan, R. J. Mol. Catal. A: Chem. 2013, 377, 1.

    CAS  Article  Google Scholar 

  9. 9.

    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.]

  10. 10.

    Kolosov, M. A.; Shvets, E. H.; Kulyk, O. G.; Orlov, V. D. Chem. Heterocycl. Compd. 2015, 51, 1052. [Khim. Geterotsikl. Soedin. 2015, 51, 1052.]

  11. 11.

    Stadler, A.; Kappe, C. O. J. Chem. Soc., Perkin Trans. 2 2000, 1363.

  12. 12.

    Silverstein, R. M.; Webster F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds [Russian translation]; BINOM. Laboratoriya znanii: Moscow, 2011, p. 364.

  13. 13.

    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.

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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''.

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Correspondence to Mikhail Krasavin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(11), 918–922

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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).

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  • aldehydes
  • tetralone
  • 1H-tetrazol-5-amine
  • Biginelli reaction
  • microwave irradiation
  • multicomponent reactions