Diastereoselective synthesis of bisspiroconjugated oxindoles by [3+2] dipolar cycloaddition

Швец, А. А.; Kurbatov, S. V.

doi:10.1007/s10593-009-0344-1

Cited by 19 publications

(7 citation statements)

References 3 publications

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“…So using the other nitrogen nucleophiles that have amphoteric and more basicity were encouraged to shift the equilibrium to formation of the spiro derivative via attacking the benzoxazinone moiety at C 2 . When the 2‐benzoxazinonyl benzoic acid (BBA) could react with some aromatic amine, for example, 4‐anisidine, 4‐amino‐acetophenone, and 2‐aminopyridine afforded the corresponding spiro derivatives 4 , 5 , and 6 (Scheme ) . The strong basicity and weak nucleophilicity could be encouraged in formation of the spiro products 1 – 6 that be supporting by NMR.…”

Section: Resultsmentioning

confidence: 99%

Ultrasonic Aptitude of Regioselective Reaction of 6‐bromo‐spiro‐3,1‐benzoxazinone2,1′‐isobenzofuran‐3′,4‐dione Towards Some Electrophilic and Nucleophilic Reagents

El‐Hashash

Rizk

El‐Badawy

2018

Journal of Heterocyclic Chem

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In the present work, the 2‐benzoxazinonyl benzoic acid (BBA) could be isomerized to the stereogenic spiro products (SBI) via ultrasonic and basic reaction conditions. The spiro compounds (SBI) have both electrophilic and nucleophilic centers. A series of nitrogen nucleophiles such as hydrazine hydrate, glycine, 2‐aminopyridine, 2‐picolinylamine, 4‐anisidine, 4‐aminoacetophenone and carbon electrophiles such as oxiranylmethylchloride, ethylchloroacetate, chloroacetylchloride, Mannich reagents, for example, formaldehyde with piperidine or morpholine can be treated with 2‐benzoxazine‐2‐yl benzoic acid (BBA) via multicomponent reaction. The basicity of previous nucleophiles can be controlled on the course of reaction of 2‐benzoxazinonyl benzoic acid. The chemical structure of the synthesized compounds can be confirmed by microanalytical, spectral data and optimized by quantum chemical parameters.

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Section: Resultsmentioning

confidence: 99%

Ultrasonic Aptitude of Regioselective Reaction of 6‐bromo‐spiro‐3,1‐benzoxazinone2,1′‐isobenzofuran‐3′,4‐dione Towards Some Electrophilic and Nucleophilic Reagents

El‐Hashash

Rizk

El‐Badawy

2018

Journal of Heterocyclic Chem

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“…Convenient dipoles for constructing pyrrolidine-(pyrrolizidine)oxindole compounds are non-stabilized azomethine ylides generated from isatins. 15,16 Given the possibility of varying the substituents at the double bond of arylmethylidene derivatives of furan-2-ones, the considered approach can be expected to be very successful in terms of creating previously unknown assemblies of heterocycles containing the dispiropyrrolidine fragment.…”

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confidence: 99%

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Anis’kov

Kamneva

Zheleznova

et al. 2015

Chem Heterocycl Comp

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“…should react with 1,3-dipoles, e.g., azomethine ylides, to form dispiro heterocycles [5,6]. In fact, 1,3-dipolar cycloaddition of compounds IV and V to azomethine ylide generated in situ from sarcosine (VI) and paraformaldehyde [7] afforded dispiro pyrrolidines VII and VIII in moderate yield (Scheme 2).…”

Section: VIIImentioning

confidence: 99%

New ylidene derivatives of pyrrolo[2,1-α]isoquinoline-2,3-dione in the synthesis of dispiropyrrolidines

et al. 2011

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SHORT COMMUNICATIONSReactions of pyrrolo[2,1-a]isoquinoline-2,3-diones with nitrogen-centered nucleophiles can be accompanied by opening of the pyrrole ring [1,2] or the latter may be conserved [3]. The Knoevenagel condensation of pyrrolo[2,1-a]isoquinoline-2,3-diones with cyanoacetic acid derivatives does not involve opening of the pyrrole ring [4]. The goal of the present work was to synthesize new ylidene derivatives of pyrrolo[2,1-a]-isoquinoline-2,3-diones and study their behavior as dipolarophiles.In continuation of our studies on reactions of pyrrolo[2,1-a]isoquinoline-2,3-dione (I) and its benzofused derivative II with nucleophiles, we examined their condensation with such sulfur-centered nucleophiles as N-substituted rhodanines IIIa and IIIb (Scheme 1). The reactions were carried out in methanol in the presence of a catalytic amount of 40% aqueous potassium hydroxide. The condensation was not accompanied by opening of the pyrrole ring, and the products were the corresponding thiazolidin-5-ylidenesubstituted derivatives IV and V.According to spectral data, compounds IV and V were formed exclusively as E isomers with trans orientation of the carbonyl groups in the pyrrole and thiazolidine rings. The 1 H NMR spectra of IV and V contained no signals assignable to other isomers, and the 1′-H (IV) and 10′-H (V) signals were displaced downfield (δ 7.15 and 7.28 ppm, respectively) due to deshielding effect of the C 4 =O carbonyl group in the rhodanine fragment.The newly formed double C=C bond is a good dipolarophile, so that ylidene derivatives IV and V

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Diastereoselective synthesis of bisspiroconjugated oxindoles by [3+2] dipolar cycloaddition

Cited by 19 publications

References 3 publications

Ultrasonic Aptitude of Regioselective Reaction of 6‐bromo‐spiro‐3,1‐benzoxazinone2,1′‐isobenzofuran‐3′,4‐dione Towards Some Electrophilic and Nucleophilic Reagents

Ultrasonic Aptitude of Regioselective Reaction of 6‐bromo‐spiro‐3,1‐benzoxazinone2,1′‐isobenzofuran‐3′,4‐dione Towards Some Electrophilic and Nucleophilic Reagents

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

New ylidene derivatives of pyrrolo[2,1-α]isoquinoline-2,3-dione in the synthesis of dispiropyrrolidines

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