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

ABSTRACT 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...

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Bibliographic Details
Published inHeteroatom chemistry Vol. 25; no. 4; pp. 226 - 237
Main Authors Fershtat, Leonid L., Struchkova, Marina I., Goloveshkin, Alexander S., Bushmarinov, Ivan S., Makhova, Nina N.
Format Journal Article
LanguageEnglish
Published LONDON Blackwell Publishing Ltd 01.07.2014
Wiley-Hindawi
John Wiley & Sons, Inc
Subjects
Acids
Chemistry
Chemistry, Multidisciplinary
Diffraction
Physical Sciences
Science & Technology
HETEROCYCLIC REARRANGEMENTS
BENZOFUROXANS
THERMOLYSIS
MECHANISM
RING
FUROXAN DERIVATIVES
NITRIC-OXIDE
CHEMISTRY
NO DONORS
FURAZAN
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Summary:ABSTRACT 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.
Bibliography:istex:57A6FDCFCB985C72194B1E0EF64566E1F8744250
Russian Academy of Sciences
ark:/67375/WNG-7ZF985BV-B
Russian Foundation for Basic Research - No. 12-03-12012 OFNM; No. 12-03-31560
ArticleID:HC21166
Contract grant numbers: 12‐03‐12012 OFNM and 12‐03‐31560.
Contract grant sponsor: Russian Academy of Sciences (the program OKhNM‐04).
Contract grant sponsor: Russian Foundation for Basic Research.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1042-7163
1098-1071
DOI:10.1002/hc.21166