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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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). https://doi.org/10.1007/s10593-017-1985-0

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Keywords

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