Synthesis of methyl 3-amino-4-aryl(or methyl)sulfonyl-2-thiophenecarboxylates from 3-alkoxy-2-aryl(or methyl)-sulfonylacrylonitriles

Authors
Stephens, CE Price, MB Sowell, JW
Citation
Ce. Stephens et al., Synthesis of methyl 3-amino-4-aryl(or methyl)sulfonyl-2-thiophenecarboxylates from 3-alkoxy-2-aryl(or methyl)-sulfonylacrylonitriles, J HETERO CH, 36(3), 1999, pp. 659-665
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
36
Issue
3
Year of publication
1999
Pages
659 - 665
Database
ISI
SICI code
0022-152X(199905/06)36:3<659:SOM3M>2.0.ZU;2-6
Abstract
The synthesis of a series of methyl 3-amino-4-aryl(or methyl)sulfonylthioph ene-2-carboxylates by reaction of 3-alkoxy-2-aryl(or methyl)sulfonylacrylon itriles with methyl thioglycolate in the presence of triethylamine is descr ibed. Hydrolysis/decarboxylation of the ester at the 2-position and acylati on of the resulting amine represents a convenient route to 4-arylsulfonyl-3 -carboxamidothiophenes. Attempted acylation of a title aminothiophene under standard conditions was unsuccessful.