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Synthesis of novel dibenzo-2,6,9-triazabicyclo[3.3.1]nonanes from o-tosylamino- and o-mesylaminobenzaldehydes

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Abstract

Condensation of o-tosylaminobenzaldehyde with γ-aminobutyric, 4-aminophenylthioacetic, and p-aminobenzoic acids and β-alanine gave 6,12-epimino-5,11-ditosyl-5,6,11,12-tetrahydrodibenzo[b, f]-1,5-diazocines with carboxyl-containing substituents at the bridging N atoms. The structures of three products were examined by X-ray diffraction analysis. Condensation of o-mesylaminobenzaldehyde (prepared by the McFadyen-Stevens reaction) with NH4OAc and primary amines afforded 6,12-epimino-5,11-dimesyl-5,6,11,12-tetrahydrodibenzo[b, f]-1,5-diazocine derivatives.

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Rostov State University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    L. Yu. Ukhin

  2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    L. G. Kuz’mina

Authors
  1. L. Yu. Ukhin
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  2. L. G. Kuz’mina
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2165–2171, October, 2004.

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Ukhin, L.Y., Kuz’mina, L.G. Synthesis of novel dibenzo-2,6,9-triazabicyclo[3.3.1]nonanes from o-tosylamino- and o-mesylaminobenzaldehydes. Russ Chem Bull 53, 2262–2268 (2004). https://doi.org/10.1007/s11172-005-0111-0

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  • DOI: https://doi.org/10.1007/s11172-005-0111-0

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