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Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/114227
Título

The reaction of 2-amino-4 H-pyrans with N-bromosuccinimide

AutorSamadi, Abdelouahid ; Silva, Daniel; Chioua, Mourad ; Infantes, L. ; Soriano, Elena ; Marco-Contelles, José
Palabras claveDFT
Reaction mechanism
N-Bromosuccinimide
2-Amino-4H-pyrans
NBS
Fecha de publicación2014
EditorSpringer
CitaciónMolecular Diversity 19: 103-122 (2014)
ResumenThe reaction of racemic 2-amino-4H-pyrans, such as 3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitriles, with N-bromosuccinimide (NBS), in CH2 Cl2, at room temperature, is a very quick, regio, stereoselective, and high yielding process, affording major racemic (1S,2S)-2-bromo-3-imino-benzo[f]chromene or racemic (1S,2S)-2-bromo-3-(bromoimino)-benzo[f]chromene derivatives, when using 1.0 or 2.2 equivalents of NBS, respectively. This reaction, extended to isomeric 2-amino-4-aryl-4H-benzo[h]chromene-3-carbonitriles, showed an unexpected reactivity, affording racemic (3S,4S)-3-bromo-2-(bromoimino)-benzo[h]chromene-3-carbonitriles or 2-oxo-2H-benzo[h]chromene-3-carbonitriles, when using 2.2 or 1.0 equivalents of NBS, respectively. The reaction of alkyl 6-amino-5-cyano-2-methyl-4H-pyran-3-carboxylates has yielded unstable racemic (3S,4S)-alkyl 3-bromo-2-(bromoimino)-3-cyano-6-methyl-3,4-dihydro-2H-pyran-5-carboxylates. The mechanism of these reactions has been investigated by computational methods.
URIhttp://hdl.handle.net/10261/114227
DOI10.1007/s11030-014-9560-4
Identificadoresdoi: 10.1007/s11030-014-9560-4
issn: 1381-1991
e-issn: 1573-501X
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