Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions

Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2016, Volume: 57, Number: 50, Pages: 5685-5689 Pages count : 5 DOI: 10.1016/j.tetlet.2016.11.023

Authors

Fershtat Leonid L. ¹ , Epishina Margarita A. ¹ , Ovchinnikov Igor V. ¹ , Struchkova Marina I. ¹ , Romanova Anna A. ^2,3 , Ananyev Ivan V. ^2,3 , Makhova Nina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991 Moscow, Russian Federation
3	Higher Chemical College, Russian Academy of Sciences, 125047 Moscow, Russian Federation

A general and simple method for the preparation of under explored 3-aryl-4-hydroxyfuroxans by nucleophilic substitution of the nitro group in 3-aryl-4-nitrofuroxans using NaOH in H2O-THF has been developed. The methylation of 3-aryl-4-hydroxyfuroxans was studied with various methylating reagents (CH2N2, MeI, (MeO)2SO2) which showed for the first time that 3-aryl-4-hydroxyfuroxans are prone to side-chain prototropic tautomerism. Furoxan derivatives of a novel type, N(5)-alkylation products (3-aryl-5-methyl-1,2,5-oxadiazol-4(2H)-one 2-oxides), were synthesized under mild conditions, along with regioselective formation of the O-alkylation products (3-aryl-4-methoxyfuroxans).

Fershtat L.L. , Epishina M.A. , Ovchinnikov I.V. , Struchkova M.I. , Romanova A.A. , Ananyev I.V. , Makhova N.N.
Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions
Tetrahedron Letters. 2016. V.57. N50. P.5685-5689. DOI: 10.1016/j.tetlet.2016.11.023 WOS Scopus OpenAlex

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