Journal ArticleDOI
One‐Pot Synthesis of Dispiro[oxindole‐3,3′‐pyrrolidines] by Three‐Component [3+2] Cycloadditions of in situ‐Generated Azomethine Ylides with 3‐Benzylidene‐2,3‐dihydro‐1H‐indol‐2‐ones
Firouz Matloubi Moghaddam,Mostafa Kiamehr,Mostafa Kiamehr,Mostafa Kiamehr,Mohammad Reza Khodabakhshi,Marjan Jebeli Javan,Shaghayegh Fathi,Alexander Villinger,Viktor O. Iaroshenko,Viktor O. Iaroshenko,Peter Langer +10 more
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TLDR
An efficient one-pot, three-component synthesis of novel dispiro[oxindole-3,3′-pyrrolidines] by 1,3-dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2-diones with sarcosine and subsequent decarboxylation, with a series of (E)-3-benzylidene-2, 3-dihydro-1H-indol-2-ones is reported as discussed by the authors.Abstract:
An efficient one-pot, three-component synthesis of novel dispiro[oxindole-3,3′-pyrrolidines] by 1,3-dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2-diones with sarcosine and subsequent decarboxylation, with a series of (E)-3-benzylidene-2,3-dihydro-1H-indol-2-ones is reported. Molecular complexity is generated in only one synthetic step. All reactions proceed with excellent regioselectivity and in good-to-excellent yields. The workup is easy, the reaction times are short, and no catalyst is required.read more
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2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides
TL;DR: This review covers the use of 2-azaallyl anions, 2-azeallyl cations, and 2-azomethine ylides in organic synthesis up through June 2018, with particular attention to both foundational studies and recent advances over the past decade involving semistabilized and nonstabilized 2-azaaranions as key intermediates in various carbon-carbon and carbon-heteroatom bond-forming processes.
Journal ArticleDOI
Synthesis and biological evaluation of new spirooxindoles with embedded pharmacophores
Sadasivam Mathusalini,Thangaraj Arasakumar,Krishnasamy Lakshmi,Chia Her Lin,Palathurai Subramaniam Mohan,Madhusudhanan Gogul Ramnath,Ramaraj Thirugnanasampandan +6 more
TL;DR: In this paper, a regioselective synthesis of new mono and bisoxindoles containing bis spiro heterocyclic hybrids has been envisaged via 1,3-dipolar cycloaddition of azomethine ylides with the dipolarophile (E)-3-((2-methoxyquinolin-3-yl)methylene)indolin-2-one, obtained through the base catalyzed condensation of indolin-1 with substituted 2-mETHoxyquinoline-3 -carbaldehyde.
Journal ArticleDOI
Regio- and diastereoselective construction of a new set of functionalized pyrrolidine, spiropyrrolidine and spiropyrrolizidine scaffolds appended with aryl- and heteroaryl moieties via the azomethine ylide cycloadditions
TL;DR: In this paper, a new set of functionalized pyrrolidines, spiro-pyrrolidine/pyrrolyl oxindoles with various aryl-and heteroaryl moieties via the azomethine ylide cycloaddition reaction are reported.
Journal ArticleDOI
Diastereoselective construction of a functionalized dihydro-pyridazine-based spirooxindole scaffold via C-3 umpolung of isatin N,N′-cyclic azomethine imine
TL;DR: An abnormal [3+3] tandem Michael addition/N-cyclization of isatin N,N′-cyclic azomethine imine 1,3-dipoles and 2-arylidene malononitrile that diastereoselectively construct a dihydro-pyridazine-based spirooxindole is demonstrated.
References
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Multicomponent Reactions with Isocyanides.
Alexander Dömling,Ivar Ugi +1 more
TL;DR: MCRs and especially MCRs with isocyanides offer many opportunities to attain new reactions and basic structures, however, this requires that the chemist learns the "language" of M CRs, something that this review wishes to stimulate.
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Asymmetric 1,3-Dipolar Cycloaddition Reactions
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Iain Coldham,Richard Hufton +1 more
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Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.
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Applications of Multicomponent Reactions to the Synthesis of Diverse Heterocyclic Scaffolds
TL;DR: This work has shown that the optimal MCR is sufficiently flexible that it can be employed to generate adducts bearing a variety of functional groups that may then be selectively paired to enable different cyclization manifolds, thereby leading to a diverse collection of products.