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Organocatalysed one-pot three component synthesis of 3,3'-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4'-indoline].

ABSTRACT: A simple and efficient methodology for the one-pot synthesis of 3,3'-disubstituted oxindoles featuring an all-carbon quaternary center has been demonstrated through l-proline catalysed three-component reaction based on sequential Knoevenagel condensation/Michael addition and also one-pot synthesis of spiro[2H-pyran-3,4'-indoline] through consecutive Knoevenagel condensation/Michael addition/reduction/cyclization reactions from readily available isatin derivatives, malononitrile, and ketones. The present methodology presents several advantages, including simple reaction set-up, short reaction times, and easy to work-up. Also, this strategy offers broad substrate scope with excellent yields and high atom economy, under mild reaction conditions.

SUBMITTER: Nichinde CB 

PROVIDER: S-EPMC10140734 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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Organocatalysed one-pot three component synthesis of 3,3'-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2<i>H</i>-pyran-3,4'-indoline].

Nichinde Chandrakant B CB   Patil Baliram R BR   Chaudhari Suryakant S SS   Mali Bhupendra P BP   Gonnade Rajesh G RG   Kinage Anil K AK  

RSC advances 20230428 19

A simple and efficient methodology for the one-pot synthesis of 3,3'-disubstituted oxindoles featuring an all-carbon quaternary center has been demonstrated through l-proline catalysed three-component reaction based on sequential Knoevenagel condensation/Michael addition and also one-pot synthesis of spiro[2<i>H</i>-pyran-3,4'-indoline] through consecutive Knoevenagel condensation/Michael addition/reduction/cyclization reactions from readily available isatin derivatives, malononitrile, and keton  ...[more]

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