Studies in the enamine field reactions of sulfonyl- and nitro-enamines with azides

Maiorana, Stefano; Pocar, Donato; Croce, Piero Dalla

doi:10.1016/s0040-4039(01)84167-8

Cited by 45 publications

(14 citation statements)

References 3 publications

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“…Ϫ Ϫ [e] The acidity of 15 at room temperature was estimated to be K a ϭ 1.6·10 Ϫ5 , which corresponds to pK a ϭ 4.8. [54] It is true that solvation would modify the stability of the different species in equilibrium. As is shown in Table 2, the 1H tautomers 1a and 4a have much larger dipole moments than their 2H counterparts 1b and 4b, which explains why both tautomers have similar stabilities in solution.…”

Section: Aqueous Basicity Measurements (Pk Bh؉ )mentioning

confidence: 99%

Basicity of N-H- and N-Methyl-1,2,3-triazoles in the Gas Phase, in Solution, and in the Solid State − An Experimental and Theoretical Study

et al. 2001

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Keywords: Ab initio calculations / Crystal structure / FT-ICR basicity / Tautomerism / 1,2,3-TriazolesThe gas-phase and aqueous basicities of six 1,2,3-triazoles have been determined, the former by FT-ICR and the latter by spectrophotometry and 1 H NMR. The gas-phase experiments agree very well with the Gibbs free energies calculated at the B3LYP/6-31G* level. In contrast, only semiquantitative ascertainments are possible when basicities in the gas phase and in solution are compared. It is possible, with the aid of calculations, to obtain a complete picture of the complex equilibria involved in C-substituted N-H-1,2,3-tria-

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Section: Aqueous Basicity Measurements (Pk Bh؉ )mentioning

confidence: 99%

Basicity of N-H- and N-Methyl-1,2,3-triazoles in the Gas Phase, in Solution, and in the Solid State − An Experimental and Theoretical Study

et al. 2001

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“…One of the well-known reactions of organic alkynes with azide can afford trizoles via cycloaddition [ 40 ]. The chemistry of the 1,3-dipolar cycloaddition of azides and alkynes is widely used in applications in organic, materials, and medicinal chemistry [ 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 ]. Ruthenium vinylidene complex 2e containing an alkyl group at Cγ and reacting with TMSN 3 yielded an N -coordinated complex as the major product.…”

Section: Resultsmentioning

confidence: 99%

Reactivity of Ruthenium Vinylidene Complexes Containing Indenyl/dppe Ligands and Unsaturated Bonds at Cd with Trimethylsilyl Azide

Sung

Her

et al. 2012

Molecules

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This study presents a new reaction of cationic vinylidene complexes with Me3SiN3 (TMSN3), which yields N-coordinated nitrile complexes 3. Treatment of a ruthenium acetylide precursor containing indenyl and dppe ligands with a series of organic halides produced the corresponding vinylidene complexes 2 in good yield. Further reaction of 2 with TMSN3 at room temperature produced N-coordinated ruthenium nitrile complexes 3. Unlike the reaction of cyclopropenylruthenium complexes with TMSN3, which yielded different products depending on the substituent at Cγ, the vinylidene complexes containing unsaturated bonds at Cδ yielded similar N-coordinated nitrile complexes. This transformation did not seemingly occur in the reaction of ruthenium vinylidene complexes containing Cp and PPh3 ligands with TMSN3. Deprotonation of these vinylidene complexes yielded cyclopropenyl or thermodynamic furylruthenium complexes, depending on the substitute at Cγ. Subsequent reactions of the cyclopropenyl or furylruthenium complexes with TMSN3 afforded different products.

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“…5‐Amino‐triazolines 2 bearing at position 1 carboxylic, phosphoryl and sulfonyl groups can undergo elimination of the corresponding amides to 1‐ N ‐unsubstituted 1,2,3‐triazoles 4 (direction B in Scheme ) . These reactions were used to prepare 1,2,3‐triazoles bearing electron‐withdrawing substituents at position 4 of the ring, such as nitro, arylsulfonyl and carbonyl groups (Scheme ).…”

Section: Ring Transformations Of 5‐amino‐123‐triazolinesmentioning

confidence: 99%

The Rich Chemistry Resulting from the 1,3‐Dipolar Cycloaddition Reactions of Enamines and Azides

et al. 2017

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Enamines exhibit exceptionally high reactivity in their 1,3‐dipolar cycloaddition reactions with azides in comparison with other dipolarophiles. This review includes the reactions of various types of enamines with azides of different nature, including catalytic processes. The initial products of the reaction, 1,2,3‐triazolines, are generally unstable and very reactive compounds which are prone to undergo various ring transformations. This provides the background for new synthetic methods and novel reaction types. The formation of a variety of products derived from the reaction of enamines with azides such as mono‐, di‐and tri‐substituted 1,2,3‐triazoles, including N‐unsubstituted derivatives, fused, conjugated and spiro heterocycles, two types of amidines and diaminoalkenes are classified in this review according to the type of stabilization/transformation of the intermediate triazolines.

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Studies in the enamine field reactions of sulfonyl- and nitro-enamines with azides

Cited by 45 publications

References 3 publications

Basicity of N-H- and N-Methyl-1,2,3-triazoles in the Gas Phase, in Solution, and in the Solid State − An Experimental and Theoretical Study

Basicity of N-H- and N-Methyl-1,2,3-triazoles in the Gas Phase, in Solution, and in the Solid State − An Experimental and Theoretical Study

Reactivity of Ruthenium Vinylidene Complexes Containing Indenyl/dppe Ligands and Unsaturated Bonds at Cd with Trimethylsilyl Azide

The Rich Chemistry Resulting from the 1,3‐Dipolar Cycloaddition Reactions of Enamines and Azides

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