One-pot synthesis of nitrones from nitro compounds by in situ trapping of arylhydroxylamines

One-pot synthesis of nitrones from nitro compounds by in situ trapping of arylhydroxylamines

Highly efficient, convenient, simple procedure and a highly chemoselective method has been described for the conversion of nitroarenes to their corresponding nitrone derivatives by employing SnCl 2 ·2H 2 O and Na 2 CO 3 in the grinding apparatus in solvent-free conditions. Biaryl nitrones can be ach...

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Bibliographic Details
Published in:Monatshefte für Chemie Vol. 148; no. 6; pp. 1101 - 1107
Main Authors: Kazemi, Foad, Ramdar, Moosa, Tavana, Bahram, Davarpanah, Jamal
Format: Journal Article
Language:English
Published: Vienna Springer Vienna 01-06-2017
Springer Nature B.V
Subjects:
Analytical Chemistry
Aromatic compounds
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Condensation
Derivatives
Grinding
Inorganic Chemistry
Nitro compounds
Organic Chemistry
Original Paper
Physical Chemistry
Reduction
Theoretical and Computational Chemistry
One-pot synthesis
Reduction
Solid phase synthesis
Nitroarenes
Arylhydroxylamine
Nitrone
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Description
Summary:Highly efficient, convenient, simple procedure and a highly chemoselective method has been described for the conversion of nitroarenes to their corresponding nitrone derivatives by employing SnCl 2 ·2H 2 O and Na 2 CO 3 in the grinding apparatus in solvent-free conditions. Biaryl nitrones can be achieved via the condensation of an aldehyde with an unstable arylhydroxylamine which is prepared in situ through the reduction of the corresponding nitro aromatic compound. Interestingly, the slow and nonselective reduction of nitroarene to arylhydroxylamine step was directed with the condensation of in situ-prepared arylhydroxylamine with aromatic aldehyde (second step). Moreover, this protocol was successfully used for preparation of valuable dinitrones from dialdehyde and nitro aromatic compounds. For dinitrone preparation, dialdehyde compounds were first synthesized by the reaction of salicylaldehyde and glycol derivatives. Then, dialdehydes were reacted with reduced nitro compounds in optimal conditions that we used for synthesis of biaryl nitrones. Graphical Abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-016-1896-2