Complementary heterogeneous/homogeneous protocols for the synthesis of densely functionalized benzo[d]sultams: C-C bond formation by intramolecular nucleophilic aromatic fluorine displacement.
Polyfunctionalized benzo[d]sultams 7 and 8, which contain an alpha-amino acid unit, have been synthesized from the corresponding open chain (pentafluorobenzene)sulfonamides 4 by complementary solid-liquid phase transfer catalysis (SL-PTC) and homogeneous protocols. The cyclization step proceeds through the intramolecular nucleophilic displacement of an aromatic fluorine atom.
Penso
Michele
M
CNR-Istituto di Scienze e Tecnologie Molecolari, Via Golgi 19, Milano, Italy. michele.penso@istm.cnr.it
Albanese
Domenico
D
Landini
Dario
D
Lupi
Vittoria
V
Tagliabue
Aaron
A
D000097:Acetonitriles / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D005461:Fluorine / Q000737:chemistry; D005464:Fluorobenzenes / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D008956:Models, Chemical; D013449:Sulfonamides / Q000138:chemical synthesis*
D000097:Acetonitriles; D000596:Amino Acids; D005464:Fluorobenzenes; D006847:Hydrocarbons, Iodinated; D013449:Sulfonamides; C480101:beta-sultam; D005461:Fluorine; D002244:Carbon; C014055:methyl iodide