Oxidative nucleophilic substitution of hydrogen versus ring-opening in the reaction of 4-R-2-nitrothiophenes with amines. The crucial effect of 4-alkyl groups.
J Org Chem
; 72(15): 5771-7, 2007 Jul 20.
Article
em En
| MEDLINE
| ID: mdl-17595137
ABSTRACT
4-Alkyl-2-nitrothiophenes [10 R = CH3, CH(OH)CH3, CH(OCH3)CH3] react with secondary aliphatic amines, in the presence of AgNO3, to give 3-alkyl-2-amino-5-nitrothiophenes (12) through an oxidative nucleophilic substitution of hydrogen (ONSH) of synthetic interest. This behavior is in striking contrast with that of the parent 2-nitrothiophene (6), which was found to undergo ring-opening in analogous reaction conditions. A possible rationale for the crucial effect of alkyl groups is suggested, grounded also on a study of the corresponding Meisenheimer-like adducts.
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MEDLINE
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En
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J Org Chem
Ano de publicação:
2007
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Article