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One‐pot synthesis of new spiro[cyclopropane‐1,3′‐[3 H ]indol]‐2′(1′ H )‐ones from 3‐phenacylideneoxindoles
Author(s) -
Shaabanzadeh Masoud,
Khabari Faranak
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.394
Subject(s) - cyclopropane , diastereomer , cyclopropanation , chemistry , oxindole , hydrazine (antidepressant) , stereochemistry , organic chemistry , medicinal chemistry , catalysis , ring (chemistry) , chromatography
In a one‐pot procedure, the 3‐phenacylideneoxindoles 1a , 1b , 1c , 1d were reacted with hydrazine and then in situ with lead(IV) acetate and new diastereoisomers of spiro[cyclopropane‐1,3′‐[3 H ]indol]‐2′(1′ H )‐ones were prepared. Compounds 1a , 1b , 1c , 1d underwent a highly diastereoselective cyclopropanation leading to diastereoisomers 2a , 2b , 2c , 2d . These new compounds containing both 2‐oxindole and cyclopropane moieties may be valuable in medicinal chemistry. J. Heterocyclic Chem., (2010).