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Cycloisomerization of Oxindole‐Derived 1,5‐Enynes: A Calcium(II)‐Catalyzed One‐Pot, Solvent‐free Synthesis of Phenanthridinones, 3‐(Cyclopentenylidene)indolin‐2‐ones and 3‐Spirocyclic Indolin‐2‐ones
Author(s) -
Yaragorla Srinivasarao,
Pareek Abhishek,
Dada Ravikrishna
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700569
Subject(s) - cycloisomerization , chemistry , oxindole , isomerization , regioselectivity , cycloaddition , atom economy , catalysis , combinatorial chemistry , organic chemistry
Calcium‐catalyzed regioselective synthesis of oxindole‐derived 1,5‐enynes, followed by cycloisomerization, from readily accessible 3‐hydroxy‐3‐(alkynyl)indolin‐2‐ones and styrenes in one‐pot, under solvent‐free conditions is described. This method offers the synthesis of diverse molecules: phenanthridinones, 3‐(cyclopentenylidene)indolin‐2‐ones, and 3‐spirocyclic indolin‐2‐ones are obtained through cascade reactions including cross‐dehydrative‐coupling, [3,3]‐sigmatropic rearrangement, carbocyclization, isomerization, oxidative‐ring rearrangement, and Diels‐Alder cycloaddition. In addition, this method features atom‐ and step‐economy, broad substrate scope, and high yields.