Reaction of isatin with alkylating agents with acidic methylenes

Shmidt, María S.; Perillo, Isabel A.; González, Mercedes; Blanco, María M.

doi:10.1016/j.tetlet.2012.03.010

Cited by 28 publications

(12 citation statements)

References 17 publications

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“…A careful screening of bases revealed that potassium afforded the product in better yields. The main problem is that the N- alkylated spiro epoxyoxindole 4 is accompanied by the formation of spiro epoxyoxindole 3 even if equivalent reactants are used, which is consistent with the recently reported reactions of isatins with alkylating agents having an acidic methylene group by Blanco et al [19]. To our delight, the spiro epoxyoxindole 3 could be selectively obtained in 85% yield when the reaction was carried out in the system of K 2 CO 3 /CHCl 3 at about 50 °C for 10 h. On the other hand the N- alkylated spiro epoxyoxindole 4 was also successfully prepared in 90% yield in this system when more than two equivalents of phenacyl bromide were utilized.…”

Section: Resultssupporting

confidence: 87%

“…These fascinating spiranic frameworks can serve as important building blocks in organic synthesis for the synthesis of large-ring heterocycles [10–13]. As a consequence, in recent years much attention has been paid to the diastereoselective and enantioselective synthesis of versatile spiro-oxirane-oxindoles [14–19]. With the aim of expanding our previous studies on the synthesis of various spirooxindoles [20–25], we decided to systematically investigate the Darzens reactions of a series of isatins with phenacyl bromides and report the facile synthesis of versatile spiro[indoline-3,2'-oxiran]-2-ones.…”

Section: Introductionmentioning

confidence: 99%

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Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction

Fu¹,

Yan²

2013

Beilstein J. Org. Chem.

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SummaryA series of functionalized spiro[indoline-3,2'-oxiran]-2-ones was efficiently synthesized by Darzens reaction of phenacyl bromides with isatins both with N-alkyl groups and without N-substituent in the presence of potassium carbonate as a base catalyst. When two equivalents phenacyl bromides were used in the reaction, the N-substitution reaction of isatin also finished with the formation of spiro-oxirane-oxindoles.

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Section: Resultssupporting

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction

Fu¹,

Yan²

2013

Beilstein J. Org. Chem.

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“…IR spectra were recorded with Shimadzu 470 Infrared Spectrophotometer (KBr wafer technique). 1 H and 13 C NMR spectra were taken with a NMR LA 400 (Joel) (400 and 100 MHz respectively) with TMS as internal standard. Mass spectrometric analysis was recorded with Joel-JMS 600.…”

Section: Methodsmentioning

confidence: 99%

Investigation and Synthesis of Some Novel Spiro Heterocycles Related to Indoline Moiety

2014

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Reactions of indole-2,3-dione 1 with 2-mercaptobenzimidazole, o-phenylenediamine, 2-aminophenol, 2-aminobenzothiazole, 2-aminobenzimidazole and 3-methyl-1-phenyl-2-pyrazolin-5-one were carried out to give compounds spiroindolethiazetobenzimidazole 2, spirobenzimidazole(oxazole)indoline 3a,b, benzothiazol(imidazol) iminoindolinone 4a,b and methyloxoindolylidenepyrazolone 5 respectively. Compound 5 was reacted with 2-aminophenol as well as o-phenylenediamine to give new spirooxazepine and diazepine derivatives 6a,b respectively. Reaction of 5 with nitrogen nucleophiles as well as carbon nucleophiles was investigated to furnish new spiro heterocycles 7-11. The reaction of 2-(2-oxo-1,2-dihydroindol-3-ylidene)malononitrile compound 12 with 3-methyl-1-phenyl-2-pyrazoline-5-one was carried out to give spiroindolopyranopyrazolo derivative 13. Compounds 4a,b was reacted with thioglycolic acid to give thiazolidinone derivatives 14a,b. Epoxidation of 5 using monoperoxyphthalic acid magnesium salt hexahydrate and hydrogen peroxide were executed to afford the novel dispiro (2-pyrazolin oxiraneindoline)dione compound 15. The chemical structures of the synthesized compounds were well established by elemental and spectral analyses.

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“…Its structure allows for electrophilic substitution reactions of the aromatic ring, acylating or alkylating the NH group, and the selective reduction or condensation in two chemically distinct carbonyls. [1][2][3][4][5][6][7] The 1,3-dipolar cycloaddition reaction between the regioselective organic azides and the terminal alkynes catalyzed by copper(I) is currently the most commonly used method for obtaining 1H-1,2,3-triazoles, which are heterocycles of exclusively synthetic origin. 8 This class of compounds also has several applications in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-Assisted Synthesis of Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

Silva¹,

Pinto²,

Silva³

et al. 2016

Journal of the Brazilian Chemical Society

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This short report describes the preparation of twelve isatin derivatives, 5'-(4-alkyl/aryl-1H-1,2,3-triazoles), using 5-azido-spiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one in the presence of various alkynes under acidic conditions and ultrasound irradiation. Compared with conventional methods, yields increased to 78-98%, and reaction times decreased to 5 min. Besides time and energy saving, there was no need for purification of the product by column chromatography on silica gel, generating less waste and spent solvent.

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Reaction of isatin with alkylating agents with acidic methylenes

Cited by 28 publications

References 17 publications

Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction

Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction

Investigation and Synthesis of Some Novel Spiro Heterocycles Related to Indoline Moiety

Ultrasound-Assisted Synthesis of Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

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