Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 75, Pages 9542-9545Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc02884g
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Funding
- Science and Engineering Research Board (SERB) New Delhi [CRG/2020/000801]
- Council of Scientific and Industrial Research (CSIR), New Delhi (India)
- University Grant Commissions (UGC), New Delhi (India)
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In this study, a novel stereoselective synthesis of 2H-isoindolin-1,3-ylidenes from 2-(formylphenyl)acrylates and phenacylazide in the presence of piperidine was successfully demonstrated. The one-pot tandem reaction provides a simple and efficient method to access highly functionalized ethyl (Z)-2-((Z)-3-(2-oxo-2-arylethylidene)-2,3-dihydro-1H-benzo[e]isoindol-1-ylidene)-acetates in good to excellent yields (up to 91%), and is compatible with a wide variety of functional groups.
Here in the present manuscript, we report our observation of an unprecedented stereoselective synthesis of 2H-isoindolin-1,3-ylidenes from 2-(formylphenyl)acrylates and phenacylazide in the presence of piperidine. Unlike in our previous findings, in which we accessed 3-keto-isoquinolines from the same starting materials under slightly modified reaction conditions, this unexpected one-pot tandem reaction allows an efficient and simple method to access a variety of highly functionalized ethyl (Z)-2-((Z)-3-(2-oxo-2-arylethylidene)-2,3-dihydro-1H-benzo[e]isoindol-1-ylidene)-acetates in very good to excellent yields (up to 91%). The present methodology is compatible with a wide variety of functional groups.
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