133111-29-2Relevant academic research and scientific papers
Gold(I)-Catalyzed N-Desulfonylative Amination versus N-to-O 1,5-Sulfonyl Migration: A Versatile Approach to 1-Azabicycloalkanes
Miaskiewicz, Solène,Gaillard, Boris,Kern, Nicolas,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
, p. 9088 - 9092 (2016/07/26)
Valuable 1-azabicycloalkane derivatives have been synthesized through a novel gold(I)-catalyzed desulfonylative cyclization strategy. An ammoniumation reaction of ynones substituted at the 1-position with an N-sulfonyl azacycle took place in the presence of a gold cation by intramolecular cyclization of the disubstituted sulfonamide moiety onto the triple bond. Depending on the size of the heterocyclic ring and substitution of the substrates, two unprecedented forms of nucleophilic attack on the sulfonyl group were exploited, that is, a N-desulfonylation in the presence of an external protic O nucleophile (37–87 %, 10 examples) and a unique N-to-O 1,5-sulfonyl migration (60–98 %, 9 examples).
SUBSTITUTED PYRROLE COMPOUNDS AND USE THEREOF IN PHARMACEUTICAL COMPOSITIONS
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, (2008/06/13)
The invention concerns substituted pyrrole compounds and their pharmaceutical applications. The compounds of the invention are potent inhibitors of lipoxygenase and cyclo-oxygenase and therefore are suitable to treat the set of rheumatic illnesses and to prevent allergically induced ailments. The compounds have the general formula: STR1 where R1 denotes a C1 -C12 alkyl group, R2 denotes a hydrogen atom or a C1 -C12 alkyl group, or R1 and R2 together with the carbon atom and the nitrogen atom to which they are bound form a ring of 5 to 8 links which may contain a sulfur heteroatom or a carbonyl group and may be substituted with one or two C1 -C4 alkyl groups, each time two of the residues R3, R4 and R5 independently from one another represent a hydrogen atom, a C5 -C8 cycloalkyl group, a C1 -C12 alkyl group or an aryl group which may be substituted by one or two residues selected from a halogen atom, a nitro-, a C1 -C4 alkoxy-, a hydroxy-, a C1 -C4 alkyl- or phenoxy-group, and where the third of the residues R3, R4 and R5 denotes --CHO, --CO2 H, --COSC1 -C4 -alkyl or A--X, with A being a straight-chain or a branched C1 -C8 alkylene group which may be interrupted by an oxygen heteroatom or a carbonyl group or being a C2 -C8 alkenylene group, X being CO2 H, SO3 H, CHO, OH or SH, as well as their pharmaceutically compatible salts and esters, for pharmaceutical applications.
