ARYLSULFONYLPYRROLES FROM REACTION OF TOSYLMETHYL ISOCYANIDE (TOSMIC)WITH 3-ARYLSULFONYL ACRYLATES AS MICHAEL ACCEPTORS

Authors
DISANTO R COSTI R MASSA S ARTICO M
Citation
R. Disanto et al., ARYLSULFONYLPYRROLES FROM REACTION OF TOSYLMETHYL ISOCYANIDE (TOSMIC)WITH 3-ARYLSULFONYL ACRYLATES AS MICHAEL ACCEPTORS, Synthetic communications, 28(10), 1998, pp. 1801-1815
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
28
Issue
10
Year of publication
1998
Pages
1801 - 1815
Database
ISI
SICI code
0039-7911(1998)28:10<1801:AFROTI>2.0.ZU;2-7
Abstract
Ethyl 3-(arylthio)acrylates did not react with a-alkali metalated tosy lmethyl isocyanide (TosMIC) to afford 4-(arylthio)pyrrole-3-carboxylic acid ethyl esters. Oxidation of thioethers to sulfones generated reac tive 3-(arylsulfonyl) acrylates, which promptly underwent cycloadditio n with TosMIC in the presence of base giving ethyl 4-(arylsulfonyl)pyr role-3-carboxylates. Contrary to expectation, the use of ethyl 3-(5-ch loro-2-nitrophenylsulfonyl)acrylate led to ethyl ester of 5-tosylpyrro le-3-carboxylic acid instead of the expected ethyl hloro-2-nitrophenyl sulfonyl)pyrrole-3-carboxylate.