Abstract
Reaction of 1,10-bis(methoxymethyl)-1,10-diaza-18-crown-6 (1) with trimethylsilyl azide resulted in hitherto unknown 1,10-bis(azidomethyl)-1,10-diaza-18-crown-6 (2) and novel ionic compound 1,10-bis(azide anion)-1,10-dihydro-1,10-diaza-18-crown-6 (3). Compound 2 rnneacted with dimethyl acetylenedicarboxylate to give 1,10-bis(4,5-dimethoxycarbonyltriazolomethyl)-1,10-diaza-18-crown-6 (4). Carbamoylation of 1,10-diaza-18-crown-6 (5) with optically active α-phenylethyl amine yielded optically active 1,10-bis(α-phenylethylcarbamoyl)-1,10-diaza-18-crown-6 (6).
References
O. G. Nabiev, Z. O. Nabizade, R. G. Kostyanovsky, Mendeleev Commun., 2009, 19, 281.
I. S. Bushmarinov, O. G. Nabiev, R. G. Kostyanovsky, M. Yu. Antipin, K. A. Lyssenko, CrystEngComm, 2011, 13, 2930.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0772–0774, March, 2014.
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Kostyanovsky, R.G., Lyssenko, K.A., Nabiev, O.G. et al. Novel 1,10-diaza-18-crown-6 derivatives. Russ Chem Bull 63, 772–774 (2014). https://doi.org/10.1007/s11172-014-0507-9
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DOI: https://doi.org/10.1007/s11172-014-0507-9
Key words
- 1,10-diaza-18-crown-6
- 1,10-bis(methoxymethyl)-1,10-diaza-18-crown-6
- 1,10-bis(azidomethyl)-1,10-diaza-18-crown-6
- 1,10-bis(azide anion)-1,10-dihydro-1,10-diaza-18-crown-6
- 1,10-bis(4,5-dimethoxycarbonyltriazalomethyl)-1,10-diaza-18-crown-6
- trimethylsilyl azide
- aminomethyl-substituted triazoles
- dimethyl acetylenedicarboxylate