Selective transformations of isatins to substituted 2-oxindoles

Macaev, Fliur; Sucman, Natalia; Boldescu, Veaceslav

doi:10.1007/s11172-014-0389-x

Cited by 8 publications

(3 citation statements)

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“…Due to accessibility, as well as green considerations, enantioselective organocatalysis has proved to be one of the most efficient approach towards the synthesis of drugs and natural products [39][40][41][42][43]. In particular, the organocatalytic functionalization of indolin-3-one has been recently studied since this type of heterocycles are commonly found in an ample range of biologically active natural alkaloids [44][45][46][47][48]. As depicted in Scheme 4 (Equation (a)), the 2-catalyzed electrophilic α-amination of methyl 1-acetyl-3-oxoindoline-2-carboxylate [49] in ChCl/glycerol (1/2) as solvent under the optimized reaction conditions gave compound 15 in excellent yields and moderate enantioselectivities (15a: R = iPr, 30% ee; 15b: R = tBu, 45% ee).…”

Section: Resultsmentioning

confidence: 99%

Deep Eutectic Mixtures as Reaction Media for the Enantioselective Organocatalyzed α-Amination of 1,3-Dicarbonyl Compounds

et al. 2018

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The enantioselective α-amination of 1,3-dicarbonyl compounds has been performed using deep eutectic solvents (DES) as a reaction media and chiral 2-amino benzimidazole-derived compounds as a catalytic system. With this procedure, the use of toxic volatile organic compounds (VOCs) as reaction media is avoided. Furthermore, highly functionalized chiral molecules, which are important intermediates for the natural product synthesis, are synthetized by an efficient and stereoselective protocol. Moreover, the reaction can be done on a preparative scale, with the recycling of the catalytic system being possible for at least five consecutive reaction runs. This procedure represents a cheap, simple, clean, and scalable method that meets most of the principles to be considered a green and sustainable process.

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Section: Resultsmentioning

confidence: 99%

Deep Eutectic Mixtures as Reaction Media for the Enantioselective Organocatalyzed α-Amination of 1,3-Dicarbonyl Compounds

et al. 2018

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“…The construction of spirocyclic oxindole-butenolides involves a formation vinyltriphenylphosphonium salt [4,38,39] and concomitant addition to activated carbonyl atom of starting isatins. …”

Section: Introductionmentioning

confidence: 99%

The Synthesis of New Spirolactones from Substituted Isatins

Sucman¹,

Pogrebnoi²,

Обушак³

et al. 2015

ChemJMold

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Abstract. Interaction of N-ethyl isatin 3 with dimethyl acetylenedicarboxylate in the presence triphenylphosphine has led to good selectivity of methyl 1'-ethyl-4-methoxy-2',5-dioxo-5H-spiro[furan-2,3'-indoline]-3-carboxylate 4 formation. Similar yields of spirolactones 6,8 were obtained by addition of dimethyl acetylenedicarboxylate to 5-bromo functionalized isatins 5,7. However, reaction of N-butyl isatin 9 resulted in formation of an inseparable mixture of compounds. Treatment of N-benzyl isatin 10 and dimethyl acetylenedicarboxylate with triphenylphosphine proceeded with reduced selectivity of the spirooxindole 11 formation.Keywords: spirolactones, isatins, triphenylphosphine, dimethyl acetylenedicarboxylate. IntroductionThe widespread distribution of butenolides in naturally occurring [1-3] and synthetic bioactive substances strongly motivate an interest for improving the methodology of the selective synthesis of butenolide functionalized spirooxindoles in high yield [4,5]. Such developments are of interest not only for the possible total synthesis of therapeutically useful spirooxindoles [6][7][8][9][10][11][12][13][14][15], but also for the preparation of synthetic analogs [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] in order to improve our knowledge in structure-activity relationships [12-14, 31, 32]. So-called butenolide functionalized spirooxindoles 1 provide the most interesting subject for synthetic investigations in view of the large and ever increasing number of the members of this family which have furan-2(5H)-one 2 as a building block (Scheme 1).

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“…The use of exocyclic olefins enables the construction of functionalised five-membered spiro heterocycles. [5][6][7][8][9][10][11] N-Arylpyrazoles are a very exciting class of heterocyclic compounds that have potent pharmacological activities in many medical fields such as hypoglycemic, 12 antibacterial, antifungal, 13 antitumor, 14 anti-thromboembolic disorders, antiangiogenic 15 and anti-inflammatory effects. 16,17 Pyrrolidine, pyrrolizine, and pyrrolothiazole derivatives are important bioactive heterocyclic compounds which have antimicrobial, antiviral, anti-inflammatory, antitubercular, anticancer, and antidiabetic activities.…”

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confidence: 99%