METHYLATION OF 4-NIТRO-1,2,3-TRIAZOLE IN NEUTRAL ENVIRONMENTS
Author:
Суханов Г.Т.,Филиппова Ю.В.,Крупнова И.А.,Босов К.К.,Суханова А.Г.,Пивоварова Е.В.
Abstract
Алкилирование NH-гетероцикла4-нитро-1,2,3-триазола диметилсульфатом сопровождается тандемными реакциями алкилирования–кватернизации и приводит к образованию сложной смеси продуктов N-моноалкилирования по всем трем гетероатомам N-1, N-2 и N-3 с существенным преобладанием неизвестного ранее N3-производного, а также продукта их дальнейшего превращения – соли 1,3-диметил-4-нитро-1,2,3-триазолия.Alkylation of the NH-heterocycle of 4-nitro-1,2,3-triazole with dimethyl sulfate is accompanied by tandem alkylation-quaternization reactions and leads to the formation of a complex mixture of N-monoalkylation products at all three heteroatoms N-1, N-2, and N-3 with a significant predominance previously unknown N3-derivative, as well as the product of their further conversion - 1,3-dimethyl-4-nitro-1,2,3-triazolium salts.
Publisher
Ultrasound Technology Center of Altai State Technical University
Reference12 articles.
1. (a) Pryde, D. C., et al, "Novel Selective Inhibitors of Neutral Endopeptidase for the Treatment of Female Sexual Arousal Disorder. Synthesis and Activity of Functionalized Glutaramides," J. Med. Chem., vol. 49, pp. 4409-4424.June 2006. 2. (b) Rajeev Kharb, Prabodh Chander Sharma and Mohammed Shahar Yar, "Pharmacological significance of triazole scaffold," J. Enz. Inhib. and Med. Chem., vol. 26, Issue 1, pp. 1-21, 2011. 3. Kagitani, T., Minagavana, M., Nakahara, Y., Kimura, R., Tsubakimoto, T., Oshiumi, R, and Sakano, K. Patent JP 62039525 A2, 1987, Chem. Abst. 1987, 107, 59040. 4. Millar, R.W., Hamid, J., Endsor, R., Swinton, P.F. and Cooper, J. “Selection and Synthesis of Energetic Heterocyclic Compounds Suitable for Use in Insensitive Explosive and Propellant Compositions,” Prop., Explos., Pyrotech., vol. 33, Issue 1, pp 66–72. 2008. 5. Smiglak, M., Hines, C. C., Wilson, T. B., Singh, S., Vincek, A. S., Kirichenko, K., Katritzky, A. R. and Rogers, R. D. “Ionic Liquids Based on Azolate Anions,” Chem. Eur. J., vol. 16, pp. 1572–1584. January 2010.
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