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Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine

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Abstract

A convenient preparation method was developed for 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine by substituting one nitro group of 4,4″-dinitro-3,3′:4′,3″-ter-1,2,5-oxadiazole at treating with equivalent quantity of ammonia in solvents of low polarity. In the reaction of the obtained amino-nitro derivative with N- and О- nucleophiles depending on the reaction conditions and the nucleophile nature either substitution of the nitro group occurs for the nucleophile residue to form 4″-alkoxy-, azido-, hydraznyl- or mono- and dialkylamino-[3,3′;4′,3″]-ter(1,2,5-oxadiazol)-4-ylamines, or the compound suffers an intramolecular cyclization affording 7Н-tri-1,2,5-oxadiazolo[3,4-b:3′,4′-d:3″,4″-f]azepines.

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Authors and Affiliations

  1. Special Design and Technology Bureau “Technolog,”, Sovetskii pr. 33-A, St. Petersburg, 192076, Russia

    A. A. Astrat’ev, A. I. Stepanov, V. S. Sannikov & D. V. Dashko

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  1. A. A. Astrat’ev
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  2. A. I. Stepanov
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  3. V. S. Sannikov
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  4. D. V. Dashko
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Corresponding author

Correspondence to A. I. Stepanov.

Additional information

Original Russian Text © A.A. Astrat’ev, A.I. Stepanov, V.S. Sannikov, D.V. Dashko, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 8, pp. 1201–1209.

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Astrat’ev, A.A., Stepanov, A.I., Sannikov, V.S. et al. Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine. Russ J Org Chem 52, 1194–1202 (2016). https://doi.org/10.1134/S1070428016080170

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  • DOI: https://doi.org/10.1134/S1070428016080170

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