Base controlled rongalite-mediated reductive aldol/cyclization and dimerization of isatylidene malononitriles/cyanoacetates
Title | Base controlled rongalite-mediated reductive aldol/cyclization and dimerization of isatylidene malononitriles/cyanoacetates |
Publication Type | Journal Article |
Year of Publication | 2024 |
Authors | Chaudhari, SS, Nichinde, CB, Patil, BR, Girase, AS, Krishna, GRama, Kinage, AK |
Journal | Organic and biomolecular chemistry |
Volume | 22 |
Issue | 8 |
Pagination | 1727-1732 |
Date Published | FEB |
Type of Article | Article |
ISSN | 1477-0520 |
Abstract | In this study, we developed a novel methodology involving a base-controlled, rongalite-mediated reductive/aldol reaction, followed by cyclization of isatylidene malononitriles/cyanoacetates, resulting in the synthesis of spiro[2,3-dihydrofuran-3,3 `-oxindole]. Additionally, we have disclosed a rongalite-mediated dimerization process for isatylidene malononitriles, yielding dispiro[cyclopent-3 `-ene]bisoxindole. The utilization of rongalite in this reaction serves a dual purpose, acting both as a reducing agent and a C1 synthon. The developed approach has several advantages like a simple reaction setup, a wide substrate scope, requiring less time, using water as a green solvent, no metal or catalyst is required and products can be easily isolated via filtration with excellent yields under mild reaction conditions. A novel methodology was developed for the synthesis of spiro[2,3-dihydrofuran-3,3 `-oxindole] and dispiro[cyclopent-3 `-ene]bisoxindole under mild reaction conditions using inexpensive reagents. |
DOI | 10.1039/d3ob01794j |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 3.2 |
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