- Access to Imidazolidine-Fused Sulfamidates and Sulfamides Bearing a Quaternary Center via 1,3-Dipolar Cycloaddition of Nonstabilized Azomethine Ylides
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A 1,3-dipolar cycloaddition reaction of nonstabilized azomethine ylides and cyclic N-sulfonyl imines has been developed providing a workable access to imidazolidine-fused sulfamidates, sulfamides, and benzosultams bearing a quaternary center. Distinct from the available literature, this current work enables to make entry, for the first time, into the novel imidazolidine-fused sulfamidates and sulfamides. Furthermore, the selective imidazolidine ring opening accompanied by CH2 extrusion yielded tetra-substituted sulfamidates with an aminomethyl group. In addition, imidazolidine ring opening coupled with SO2 extrusion provided synthetically useful 1,2-diamines.
- Laha, Joydev K.,Jethava, Krupal P.
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- Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles
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Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction ofN-heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins. This electrosynthetic methodology indulges a straightforward and facile approach for the construction of substituted pyrrolidines.
- Kumar, Rakesh,Banerjee, Prabal
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p. 16104 - 16113
(2021/11/18)
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- Synthesis of Mono-N-sulfonylimidazolidines by a 1,3-Dipolar Cycloaddition Strategy, as an Alternative to Selective N-Sulfonylation, and Their Ring Cleavage To Afford 1,2-Diamines
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1,3-Dipolar cycloaddition between nonstabilized azomethine ylides and N-sulfonylimines has been developed, providing practical access to mono-N-sulfonylimidazolidines. The enhanced reactivity of N-sulfonylimines as dipolarophiles towards azomethine ylides
- Laha, Joydev K.,Jethava, Krupal P.,Tummalapalli, K. S. Satyanarayana,Sharma, Sheetal
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p. 4617 - 4624
(2017/08/30)
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- Sequential two-electron oxidation of α,α′-disilylmethylamines to generate non-stabilized azomethine ylide: An ideal approach for the construction of substituted and fused pyrrolidine ring systems
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α,α′-Di(trimethylsilylmethyl)amines undergo sequential double desilylation processes, by two-electron oxidation initiated either by photoinduced electron transfer (PET) or Ag(I)F, to produce non-stabilized azomethine ylides efficiently which upon trapping with appropriate dipolarophiles give the corresponding pyrrolidines. Application of this strategy to cyclic analogue for the rapid construction of biologically important 1-azabicyclo[m,3.0]alkane framework is discussed.
- Pandey, Ganesh,Lakshmaiah,Gadre, Smita R.
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- A New and Efficient Strategy for Non-stabilized Azomethine Ylide via Photoinduced Electron Transfer (PET) Initiated Sequential Double Desilylation
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A practical approach for generating non-stabilized azomethine ylide by PTE initiation is generated.
- Pandey, Ganesh,Lakshmaiah, G.,Kumaraswamy, G.
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p. 1313 - 1314
(2007/10/02)
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