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Synthesis of α‐oxo‐sulfines in the indole series
Author(s) -
Bergman Jan,
Romero Ivan
Publication year - 2010
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.453
Subject(s) - chemistry , thionyl chloride , oxindole , indole test , nucleophile , acetonitrile , yield (engineering) , reagent , adduct , organic chemistry , chloride , medicinal chemistry , materials science , metallurgy , catalysis
Oxindole was found to react readily with thionyl chloride to give (in an excellent yield) the isolable sulfine ( 13a ), which on heating (refluxing acetonitrile) gave isoindigo ( 15a ). The dark violet 3‐sulfinato‐oxindole ( 13a ) readily reacted with 2,3‐dimethylbutadiene to give a colorless cyclo‐adduct ( 14a ). The sulfine also reacted readily with various nucleophilic reagents, thus, thioloacetic acid gave 3‐carboxymethylthiolo‐oxindole ( 23a ). J. Heterocyclic Chem., (2010).