Straightforward entry into 5-hydroxy-1-aminopyrrolines and the corresponding pyrroles from 1,2-diaza-1,3-butadienes.
The synthesis of 5-hydroxy-1-aminopyrroline-3-carboxylic acid derivatives and 5-unsubstituted-1-aminopyrrole-3-carboxylic acid derivatives from 1,2-diaza-1,3-butadienes and aldehydes is presented. These domino reactions offer the advantage of executing multistep transformation without intermediate workup procedures. The stereoselectivity of ring closure to 5-hydroxy-1-aminopyrroline-3-carboxylic acid derivatives and phenyl transposition to 2,3-diphenyl-1-aminopyrrole-3-carboxylic acid derivatives are also studied.
Attanasi
Orazio A
OA
Istituto di Chimica Organica, Università di Urbino, Piazza della Repubblica 13, 61029 Urbino, Italy.
de Crescentini
Lucia
L
Favi
Gianfranco
G
Filippone
Paolino
P
Mantellini
Fabio
F
Santeusanio
Stefania
S