Yu. A. Kvashnin, D. V. Belyaev, M. I. Kodess, M. A. Ezhikova, G. L. Rusinov, E. V. Verbitskiy, V. N. Charushin, “Two-step synthesis of indeno[1,2-b]furazanopyrazines through combination of the SNH and Heck reactions”, Mendeleev Commun., 2023, Volume 33, Issue 6,Pages 753

This article is cited in 2 papers

Communications

Two-step synthesis of indeno[1,2-b]furazanopyrazines through combination of the S_N^H and Heck reactions

Yu. A. Kvashnin^ab, D. V. Belyaev^ac, M. I. Kodess^a, M. A. Ezhikova^a, G. L. Rusinov^ab, E. V. Verbitskiy^ab, V. N. Charushin^ab

^a I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation
^c Ural Research Institute for Phthisiopulmonology, Ekaterinburg, Russian Federation

Abstract: Enamines generated in situ from aliphatic amines and acetone react with 5-(2-bromophenyl)furazano[3,4-b]pyrazines via the nucleophilic substitution of hydrogen atom of the pyrazine ring. A representative of 9H-indeno[1,2-b]furazanopyrazin-9-ylidene ring system has been accessed by exploiting the intramolecular Heck cyclization of the obtained S_N^H-product. Several compounds derived from the S_N^H reaction, namely, N-alkyl-1-[6-(2-bromophenyl)furazano[ 3,4-b]pyrazin-5-yl]prop-1-en-2-amines, proved to exhibit a bacteriostatic activity in vitro against Mycobacterium tuberculosis H₃₇Rv

Keywords: 6389676177524NNNNfurazanopyrazines, [1,2,5]oxadiazolo[3,4-b]pyrazines, intramolecular Heck reaction, C–H functionalization, S_N^H reactions, antimycobacterials, indeno[1,2-b][1,2,5]oxadiazolo[3,4-e]pyrazines..

Language: English

DOI: 10.1016/j.mencom.2023.10.004

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