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Regioselective Alcoholysis and Hydrochlorination Reactions of Spiro‐Epoxy Oxindoles at the Spiro‐Centre: Synthesis of 3,3‐Disubstituted Oxindoles and Application for Anticancer Agents
Author(s) -
Tak Raj Kumar,
Gupta Naveen,
Kumar Manish,
Kureshy Rukhsana I.,
Khan Noorul H.,
Suresh E.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801002
Subject(s) - regioselectivity , chemistry , oxindole , hydroxymethyl , epoxy , catalysis , organic chemistry , ring (chemistry) , combinatorial chemistry , medicinal chemistry
An efficient and highly regioselective Bi III catalyzed alcoholysis and Hydrochlorination reaction of spiro‐epoxy oxindole is demonstrated with alcohols and chlorine for easy access to 3,3‐disubstituted oxindoles. This protocol furnished alkyloxy and chlorinated products at the C3 spiro center of the epoxy ring in high yields up to 98 % with excellent regioselectivity > 99 %. The synthetic protocol was further exploited for the synthesis of the anti‐cancer active molecule, 1‐benzyl‐3‐(hydroxymethyl)‐3‐(phenylamino)indolin‐2‐one.