Please use this identifier to cite or link to this item: http://nopr.niscpr.res.in/handle/123456789/58506
Title: One-pot synthesis of spiro-3,4-dihydro-2H-pyrroles through tandem nucleophilic cyclisation reaction
Authors: Chandan, Nandkishor
Keywords: Pyrrole;spiro;oxime;tosyloxime;cyclization;Meldrum’s acid;tandem;nucleophilic;α,β-unsaturated ketone
Issue Date: Nov-2021
Publisher: NIScPR-CSIR, India
Abstract: A very simple and convenient one-pot synthesis of spiro-3,4-dihydro-2H-pyrrole has been developed while synthesising the 2,2,5-trisubstituted pyrrolidines. Initially, the Meldrum’s acid has been treated with ,-unsaturated ketones in presence of anhydrous carbonate base and phase transfer catalyst benzyltriethylammonium chloride in acetonitrile to afford the Michael adduct which is readily converted to the corresponding oxime using standard conditions. The crude oxime is treated directly with p-toluenesulfonyl chloride and in presence of excess organic base results in tandem nucleophilic cyclisation product spirobicyclic as spiro-3,4-dihydro-2H-pyrrole directly, instead the tosyloxime as product.
Page(s): 1522-1527
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.60B(11) [November 2021]

Files in This Item:
File Description SizeFormat 
IJC (Section B), 60B, 1522-1527 (Nov,2021).pdf2.1 MBAdobe PDFView/Open


Items in NOPR are protected by copyright, with all rights reserved, unless otherwise indicated.