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

Abstract

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.

Green synthetic investigation and spectral characterization of some spiro pyrazolidine‐based heterocycles with potential biological activity

“…[8][9][10] Moreover, pyrazole derivatives revealed many practical applications in the medicinal field as antioxidant, antidepressant, anti-influenza, anticancer activities. [11][12][13][14][15][16][17][18] In continuation of our work on pyrazolidinediones, [19][20][21][22][23][24] we report herein green synthetic investigation of some spiroheterocycles of potential biological activity.…”

Synthesis of Some New Isatin Derivatives and Identification of Their Structures

“…Isatin has recently been used as a reagent due to its various biological (anxiogenic, sedative, anticonvulsant, endogenous MAO inhibitor and potent antagonist on atrial natriuretic peptide receptor) and structural functional properties [1,[5][6][7][8]. One of the most frequently used reactions in this context is the Schiff base reaction [9,10]. Schiff bases are used as a substrat in different cyclization or replacement reactions were synthesized using different aldehyde and amine derivatives (11,12).…”

N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media

“…Table 4 obviously demonstrates that DCDBTSD is effective catalysts in terms of reaction time and yield of obtained product relative to other reported catalysts. 30 It has been reported that the spiro-oxindole heterocyclic framework is an important structural motif in biologically relevant compounds as natural products and pharmaceuticals, e.g., surugatoxin, horsfiline, spirotryprostatin A and B, elacomine, gelsemine, alstonisine and strychnofoline. 30 It has been reported that the spiro-oxindole heterocyclic framework is an important structural motif in biologically relevant compounds as natural products and pharmaceuticals, e.g., surugatoxin, horsfiline, spirotryprostatin A and B, elacomine, gelsemine, alstonisine and strychnofoline.…”