Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

Abstract

Isatin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of multi-component reactions that include isatin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of isatin as starting material in the synthesis of various organic compounds and drugs during the period from 2012 to 2015.

Recent Achievements in the Synthesis of Heterocyclic Compounds by Phthalhydrazide-Based Multicomponent Reactions

“…Therefore, synthetic strategies involving MCRs are valuable and powerful tools for the efficient and rapid synthesis of a wide variety of organic compounds. 20,21 In continuous of our previous studies on the synthesis of heterocyclic compounds and in MCRs, [22][23][24][25][26][27][28][29][30][31][32][33][34][35] it was decided to study the application of phthalhydrazide as a starting material in the MCRs based on different heterocyclic compounds.…”

Three-component synthesis of novel spiro[4H-pyran-3,3′-oxindoles] using 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

“…Interest in the properties and synthesis of spirooxindoles, general structure 1, is witnessed by the continuing flow of papers and reviews, important examples of the latter being 'Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents', 1 'Recent progress on routes to spirooxindole systems derived from isatin', 2 'Recent advances in the synthesis of biologically active spirooxindoles', 3 'Discovery of orally active anticancer candidate CFI-400945 derived from biologically promising spirooxindoles: success and challenges', 4 'Recent applications of isatin in the synthesis of organic compounds', 5 'Catalytic asymmetric synthesis of spirooxindoles: recent developments', 6 and 'Recent advances in spirocyclization of indole derivatives'. 7 We have been examining the use of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (3), a tricyclic analogue of isatin (2), for construction of spiro-3,3-oxindoles.…”

Ultrasound-assisted, ZnBr2-catalyzed regio- and stereoselective synthesis of novel 3,3′-dispiropyrrolidine bisoxindole derivatives via 1,3-dipolar cycloaddition reaction of an azomethine ylide

“…The challenges associated with the synthesis of spiro-or dispiro-heterocycles containing the 3,3′-pyrrolidinyl-spirooxindole core have made them the subject of several elegant synthetic investigations. [22][23][24][25][26][27][28][29][30][31][32] Ultrasound irradiation has increasingly been used as a powerful tool for the preparation of organic molecules either in homogeneous or in heterogeneous liquid reaction systems. 33,34 The success and advantages of this method include shorter reaction time, higher yield, higher product purity, improved selectivity, reduced side product formation, and use of milder reaction conditions when compared with conventional heating.…”