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Improved method for the synthesis of N-methyl-2-oxoalkanesulfonamides.

✍ Scribed by Juan A. Vega; Andrés Molina; Ramón Alajarín; Juan J. Vaquero; José L.García Navío; Julio Alvarez-Builla


Book ID
104225340
Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
125 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis


Absmct. A series of N-methyl-24 xoakues~~s was pepared by reaction between silyl end ethers and N-methylsulfonylimine. In all cases yields were cmpmtively higher to those obtained by a previondy &scribed procedure

The sulfonamide group is incorporated in ii variety of annpounds having therapeutical application as antibacterials, diuretics, oral antidiabetic agents and antibiotks.1 Our initial interest in the group came from the potential of 2-0x0aikanesulfonamide derivatives 3, as intermedlrtRs in the symhesis of heterooyclic drugs.

In this report we describe a general pmcedum for the symhesis of N-methyl-2-oxoalkaue subbnamide derivatives. In comparison with the unique previously reported synthetic pmeedme,2 the method is also baaed on the formation of a catbon-sulphur bond but it uses silyl enol ethers instead of enamines as enolate anion equivalents. With a variety of easily prepared shy1 en01 ethers from the corresponding ketones. we study the scope and limitation Of the pmcedure. Results are summarized in table .

The reaction was tested under diffemnt conditions and solvents. Acetonitrile was proved to be the best solvent


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