TY - JOUR
T1 - Synthesis of new 7-azabicyclo[2.2.1]heptane derivatives
AU - Marco-Contelles, José
AU - Gómez-Sánchez, Elena
AU - Samadi, Abdelouahid
AU - Soriano, Elena
AU - Valderas, Carolina
AU - Álvarez-Pérez, Mónica
AU - Do Carmo Carreiras, Mría
PY - 2010
Y1 - 2010
N2 - The synthesis of new 7-azabicyclo[2.2.1]heptane derivatives has been achieved in a four-step synthetic sequence, starting from readily available cyclohex-3-enecarboxylic acid, Curtius reaction, stereoselective bromination leading to major benzyl(cis-3, trans-4-dibromocyclohex-1-yl)carbamates (amides or sulfonamides), followed by NaH-mediated intramolecular cyclization. The synthesis and free radical cyclization of precursors 4-7, as well as the synthesis of a conformationally constrained epibatidine analogue 3 exploiting the reactivity of the 7-azabicyclo[2.2.1]hept-2-yl radical in intramolecular reactions, are described. The N-sulfonyl functional motif is the only one to afford a cyclized product when incorporated in the radical precursor.
AB - The synthesis of new 7-azabicyclo[2.2.1]heptane derivatives has been achieved in a four-step synthetic sequence, starting from readily available cyclohex-3-enecarboxylic acid, Curtius reaction, stereoselective bromination leading to major benzyl(cis-3, trans-4-dibromocyclohex-1-yl)carbamates (amides or sulfonamides), followed by NaH-mediated intramolecular cyclization. The synthesis and free radical cyclization of precursors 4-7, as well as the synthesis of a conformationally constrained epibatidine analogue 3 exploiting the reactivity of the 7-azabicyclo[2.2.1]hept-2-yl radical in intramolecular reactions, are described. The N-sulfonyl functional motif is the only one to afford a cyclized product when incorporated in the radical precursor.
KW - 7-azabicyclo[2.2.1]hept- 2-yl radical
KW - 7-azabicyclo[2.2.1]heptane derivatives
KW - Conformationally constrained epibatidine analogues
KW - Intramolecular free radical reactions
KW - N-(arylmethyl)cyclohex-3-enamines
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U2 - 10.3998/ark.5550190.0011.307
DO - 10.3998/ark.5550190.0011.307
M3 - Article
AN - SCOPUS:77953411627
VL - 2010
SP - 56
EP - 73
JO - AEU - International Journal of Electronics and Communications
JF - AEU - International Journal of Electronics and Communications
SN - 1434-8411
IS - 3
ER -