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 α-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...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-09, Vol.73 (17), p.6686-6690
Main Authors: Penso, Michele, Albanese, Domenico, Landini, Dario, Lupi, Vittoria, Tagliabue, Aaron
Format: Article
Language:English
Subjects:
Acetonitriles - chemistry
Amino Acids - chemistry
Carbon - chemistry
Catalysis
Chemistry
Combinatorial Chemistry Techniques - methods
Cyclization
Exact sciences and technology
Fluorine - chemistry
Fluorobenzenes - chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Hydrocarbons, Iodinated - chemistry
Models, Chemical
Organic chemistry
Preparations and properties
Sulfonamides - chemical synthesis
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Summary:Polyfunctionalized benzo[d]sultams 7 and 8, which contain an α-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800930g