The Chemistry of Isatin.

The chemistry of isatins: a review from 1975 to 1999

“…Isatoic anhydride can be condensed with proline in polar aprotic solvents at high temperature, or in a reaction catalyzed by the enzyme catalase, to yield a pyrrolo [1,4] benzodiazepine ring, a structural pattern found in some antineoplasic antibiotics 188 (Scheme 43).…”

“…6-Chloroisatoic anhydride can also be converted into benzodiazepinones by cyclocondensation with 2-azetidinecarboxylic acid, which reacts with ethyl isocyanoacetate, to give imidazo[1,5-a]- [1,4]benzodiazepinones [189][190][191][192] (Scheme 44).…”

Crystal structure, Hirshfeld analysis and molecular docking with the vascular endothelial growth factor receptor-2 of (3Z)-5-fluoro-3-(hydroxyimino)indolin-2-one

“…The first reports on the synthesis of isatin and isatin-based derivatives can be traced back to the first half of the 19th century (Erdmann, 1841a,b;Laurent, 1841) and almost one hundred years after those publications, the review 'The Chemistry of Isatin' showed the versatility of this molecular fragment (Sumpter, 1944). Two recent examples of this are the synthesis of 1-[(2-methylbenzimidazol-1-yl) methyl]-2-oxo-indolin-3-ylidene]amino]-thiourea, an in vitro and in silico Chikungunya virus inhibitor (Mishra et al, 2016) and 5-chloroisatin-4-methylthiosemicarbazone, an intermediate in the HIV-1 (human immunodeficiency virus type 1) RT (reverse transcriptase) inhibitor (Meleddu et al, 2017).…”

“…compound was adapted from procedures reported previously (Martins et al, 2016;O'Sullivan & Sadler, 1956;Sandmeyer, 1919;Sumpter, 1944). A glacial acetic acid catalyzed mixture of 5-fluoroisatin (3 mmol) and hydroxylamine hydrochloride (3 mmol) in ethanol (50 mL) was stirred and refluxed for 6 h. After cooling and filtering, single crystals suitable for X-ray diffraction were obtained from the ethanolic solution by solvent evaporation.…”

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

“…For example, spirotetrahydro β-carboline is amenable to a single or low dose oral treatment for malaria, Isatin and its derivatives accomplish various reactions for the synthesis of organic compounds; Schiff bases of isatin are used for their pharmaceutical properties 17 and spirooxindoles have significant biological activities. 18,19 The chemistry of isatins was reviewed for the first time by Sumpter 20 and later updated by Popp 21 and da Silva et al 22 In recent years isatin-related review articles have been published on enantioselective reactions with isatin, [23][24][25] biochemical and pharmacological characterization of isatin and its derivatives, 26 isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks, 27 recent progress on routes to spirooxindole systems derived from isatin, 28 synthesis of spiro 29 and multispiro 30 heterocyclic compounds from isatin, the use of water in the synthesis of isatin based spirocyclic compounds, 31 and synthesis of heterocyclic compounds based on isatin through 1, 3-dipolar cycloaddition reactions. 32 Considering the importance of isatin as a building block in organic synthesis, and since there is a wide range of reactions that include isatin in the synthesis of heterocyclic compounds, this review gives an overview of the synthesis of different types of spiro-fused heterocyclic scaffolds through multicomponent reactions from the year 2012 to 2015 in which one of the starting materials is isatin.…”