Dinitrogen Trioxide-Mediated Domino Process for the Regioselective Construction of 4-Nitrofuroxans from Acrylic Acids

Dinitrogen Trioxide-Mediated Domino Process for the Regioselective Construction of 4-Nitrofuroxans from Acrylic Acids Full article

Journal

Heteroatom Chemistry
ISSN: 1042-7163 , E-ISSN: 1098-1071

Output data

Year: 2014, Volume: 25, Number: 4, Pages: 226-237 Pages count : 12 DOI: 10.1002/hc.21166

Authors

Fershtat Leonid L. ¹ , Struchkova Marina I. ¹ , Goloveshkin Alexander S. ² , Bushmarinov Ivan S. ² , Makhova Nina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences; Moscow Russia
2	A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences; Moscow Russia

4-Nitrofuroxans (4-nitro-1,2,5-oxadiazole 2-oxides) were prepared by a dinitrogen trioxide–mediated domino reaction of acrylic acids under the action of NaNO2 excess in AcOH at room temperature. The reaction proceeds completely regioselectively and presents a new, simple, general, and safe method for the preparation of both 3-aryl- and 3-alkyl-4-nitrofuroxans available with difficulty before. A mechanism for the furoxan ring construction through a four-step one-pot protocol is proposed. The synthesized nitrofuroxans have been characterized by multinuclear NMR spectroscopy and X-ray powder diffraction.

Fershtat L.L. , Struchkova M.I. , Goloveshkin A.S. , Bushmarinov I.S. , Makhova N.N.
Dinitrogen Trioxide-Mediated Domino Process for the Regioselective Construction of 4-Nitrofuroxans from Acrylic Acids
Heteroatom Chemistry. 2014. V.25. N4. P.226-237. DOI: 10.1002/hc.21166 WOS Scopus OpenAlex

≡ Web of science:	WOS:000339659400002
≡ Scopus:	2-s2.0-84904164072
≡ OpenAlex:	W2155348890