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Synthesis and cyclization reactions of 2‐amino‐3‐[(methoxy‐carbonyl)methylsulfonyl]pyrroles and thiophene
Author(s) -
Stephens Chad E.,
Sowell J. Walter
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350425
Subject(s) - chemistry , bicyclic molecule , thiophene , methylene , sulfonyl , amine gas treating , organic chemistry , intramolecular force , medicinal chemistry , hydrolysis , intramolecular reaction , alkyl
The title aminopyrroles and thiophene have been prepared by condensation of methyl (cyanomethyl‐sulfonyl)acetate with various α‐amino ketones or 2‐mercaptoacetaldehyde, respectively. Subsequent cyclization of these compounds by reaction between the amine and activated methylene has led to various ester‐substituted thiazine‐ and thiadiazine‐based bicyclic derivatives. In addition, cyclization of the title compounds by intramolecular coupling of the amine and ester has led to the analogous bicyclic thiazin‐3(2 H )‐ones. Attempted hydrolysis of the ester‐substituted bicyclics to the corresponding carboxylic acids was unsuccessful.