Base controlled rongalite-mediated reductive aldol/cyclization and dimerization of isatylidene malononitriles/cyanoacetates

TitleBase controlled rongalite-mediated reductive aldol/cyclization and dimerization of isatylidene malononitriles/cyanoacetates
Publication TypeJournal Article
Year of Publication2024
AuthorsChaudhari, SS, Nichinde, CB, Patil, BR, Girase, AS, Krishna, GRama, Kinage, AK
JournalOrganic and biomolecular chemistry
Volume22
Issue8
Pagination1727-1732
Date PublishedFEB
Type of ArticleArticle
ISSN1477-0520
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.

DOI10.1039/d3ob01794j
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.2

Divison category: 
Chemical Engineering & Process Development
Organic Chemistry
Database: 
Web of Science (WoS)

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