Literature DB >> 20373746

Pyridine core activation via 1,5-electrocyclization of vinyl pyridinium ylides generated from bromo isomerized Morita-Baylis-Hillman adduct of isatin and pyridine: synthesis of 3-spirodihydroindolizine oxindoles.

Baby Viswambharan1, Kodirajan Selvakumar, Suchithra Madhavan, Ponnusamy Shanmugam.   

Abstract

An activation of the pyridine nucleus has been achieved via 1,5-electrocyclization of vinyl pyridinium ylides generated from bromo isomerized Morita-Baylis-Hillman adducts of isatin and pyridine under basic conditions. The method has been successfully applied for an efficient synthesis of a number of 3-spirodihydroindolizine-2-oxindoles, which have been found as core structure of secoyohimbane and heteroyohimbane alkaloid natural products.

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Year:  2010        PMID： 20373746     DOI： 10.1021/ol100591r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation.

Authors:  Chunliang Lu; Qing Xiao; Paul E Floreancig
Journal:  Org Lett       Date:  2010-10-20       Impact factor: 6.005

2.  Morita-Baylis-Hillman reaction of acrylamide with isatin derivatives.

Authors:  Radhey Mohan Singh; Kishor Chandra Bharadwaj; Dharmendra Kumar Tiwari
Journal:  Beilstein J Org Chem       Date:  2014-12-12       Impact factor: 2.883

3.  Titanium(IV)-catalyzed stereoselective synthesis of spirooxindole-1-pyrrolines.

Authors:  Joseph J Badillo; Carlos J A Ribeiro; Marilyn M Olmstead; Annaliese K Franz
Journal:  Org Lett       Date:  2014-12-04       Impact factor: 6.005

4.  Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition.

Authors:  Vipin Singh; Shanta Raj Lakshmi; L Raju Chowhan
Journal:  Front Chem       Date:  2022-01-11       Impact factor: 5.221

5.  Development of spiro-3-indolin-2-one containing compounds of antiproliferative and anti-SARS-CoV-2 properties.

Authors:  Nehmedo G Fawazy; Siva S Panda; Ahmed Mostafa; Benson M Kariuki; Mohamed S Bekheit; Yassmin Moatasim; Omnia Kutkat; Walid Fayad; May A El-Manawaty; Ahmed A F Soliman; Riham A El-Shiekh; Aladdin M Srour; Reham F Barghash; Adel S Girgis
Journal:  Sci Rep       Date:  2022-08-16       Impact factor: 4.996

6.  Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione.

Authors:  Yan Sun; Jing Sun; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2013-01-03       Impact factor: 2.883
  6 in total

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