ChemInform Abstract: REACTION OF N‐ACYLISATINS WITH DIAMINES

Joshi, B. S.; Likhate, M. A.; Viswanathan, N.

doi:10.1002/chin.198436233

Cited by 3 publications

(4 citation statements)

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“…However, it has been reported that with the latter two solvents a spiro benzimidazole derivative is also formed 330 . The formation of ring opened products has also been reported to occur when using alkyldiamines 331 (Scheme 79). Likewise, the reactions of 1-acylisatins and anilines 296 or N-methylanilines 332 led to ring opened products, but one report states that 4-arylthio and 4-arylsulfonylanilines react with 1-acetylisatin to furnish 3-imines 333 .…”

Section: Scheme 76mentioning

confidence: 96%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

846

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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Section: Scheme 76mentioning

confidence: 96%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

846

447

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“…The Schiff bases (a) and (b) (Scheme 1) derived from isatin and its derivatives with different amines have been studied [1, 2, 6, 8–13]. The reaction of N-acetyl, N-benzoyl, and N-tosylisatin and their Schiff base derivatives (c) and (d) (Scheme 1) with ethanol, methanol, isopropyl alcohol, allyl alcohol, TsNH 2 , pyrrolidine, and water yield products resulting from nucleophilic attack at the C-2 carbonyl that leads to heterocyclic ring cleavage [8, 14].…”

Section: Introductionmentioning

confidence: 99%

“…Isatin (indole-2,3-dione) and its derivatives have shown a wide scale of biological activities such as antibacterial [ 1 – 3 ], antifungal [ 1 , 3 – 5 ], anticonvulsant [ 2 , 6 ], anti-HIV [ 7 ], anticancer [ 1 , 2 ], antiviral [ 1 ], and enzyme inhibitors [ 2 ]. The Schiff bases (a) and (b) ( Scheme 1 ) derived from isatin and its derivatives with different amines have been studied [ 1 , 2 , 6 , 8 – 13 ]. The reaction of N-acetyl, N-benzoyl, and N-tosylisatin and their Schiff base derivatives (c) and (d) ( Scheme 1 ) with ethanol, methanol, isopropyl alcohol, allyl alcohol, TsNH 2 , pyrrolidine, and water yield products resulting from nucleophilic attack at the C-2 carbonyl that leads to heterocyclic ring cleavage [ 8 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New Schiff Bases Derived from N (1)‐Substituted Isatin with Dithiooxamide and Their Co(II), Ni(II), Cu(II), Pd(II), and Pt(IV) Complexes

Abdulghani

Khaleel²

2009

Bioinorganic Chemistry and Applications

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Three new Schiff bases of N-substituted isatin LI, LII, and LIII = Schiff base of N-acetylisatin, N-benzylisatin, and N-benzoylisatin, respectively, and their metal complexes C1a,b = [Co2(LI)2Cl3]Cl, C2 = [Ni(LI)2Cl2]0.4BuOH, C3 = [CuLICl(H2O)]Cl ⋅ 0.5BuOH, C4 = [Pd(LI)2Cl]Cl, C5 = [Pt(L1)2Cl2]Cl2 ⋅ 1.8EtOH.H2O, C6a = [CoLIICl]Cl ⋅ 0.4H2O ⋅ 0.3DMSO, C6b = [CoLIICl]Cl ⋅ 0.3H2O ⋅ 0.1BuOH, C7 = [NiLIICl2], C8 = [CuLII]Cl2 ⋅ H2O , C9 = [Pd(LII)2]Cl2, C10 = [Pt(LII)2.5Cl]Cl3, C11a = [Co(LIII)]C12 ⋅ H2O, C11b = [Co(LIII)]Cl2 ⋅ 0.2H2O, and C12 = [Ni(LIII)2]Cl2, C13 = [Ni(LIII)2]Cl2 were reported. The complexes were characterized by elemental analyses, metal and chloride content, spectroscopic methods, magnetic moments, conductivity measurements, and thermal studies. Some of these compounds were tested as antibacterial and antifungal agents against Staphylococcus aureus, Proteus vulgaris, Candida albicans, and Aspergillus niger.

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“…[4][5][6] The Schiff bases and spiro-thiadiazoline derivatives of isatins have shown remarkable biological activities. 7,8 Therefore, design and consequent synthesis of such lactam based compounds as drugs candidates have been receiving a considerable attention in the field of medicinal organic chemistry. 9,10 The introduction of fluorine in heterocycles is known to modify the course of the reaction beside influencing the biological activity.…”

Section: Introductionmentioning

confidence: 99%

The Effect of Deactivating Groups in the Formation of Some Biologically Important Lactams (Isatins) and their Further Derivatization

Hossain

Ferdous

Muhib

et al. 2012

J. Bangla. Chem. Soc.

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Treatment of different aromatic primary amines (7a-b) with chloral hydrate and hydroxylamine hydrochloride under microwave (MW) conditions afforded corresponding isonitrosoacetanilides (6a-b). These intermediate compounds (6a-b) were cyclized in conc.H 2 SO 4 medium to give cyclic amides (5a-b) by means of elcetrophilic aromatic substitution reaction. The microwave (MW) mediated treatment of compound 5a with thiosemicarbazide afforded the corresponding Schiff-base 4a, which undergoes cyclization to give thiadiazoline (1). Beside, compound 4a was also treated with aq KOH solution under MW condition to give triazinothione (3). The Sn-HCl mediated reduction of compound 3 afforded the corresponding 6-aminothione (2). On the other hand, compound 5b was treated with o-phenylenediamine under MW condition to give the corresponding quinoxaline derivative 4b in excellent yield.

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ChemInform Abstract: REACTION OF N‐ACYLISATINS WITH DIAMINES

Abstract: Bei der Umsetzung der Acylisatine (I) mit den Phenylendiaminen (II) entstehen die Chinoxalinone (III), die zum Teil zu (IV) acylien werden.

Cited by 3 publications

References 0 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

Synthesis and Characterization of New Schiff Bases Derived from N (1)‐Substituted Isatin with Dithiooxamide and Their Co(II), Ni(II), Cu(II), Pd(II), and Pt(IV) Complexes

The Effect of Deactivating Groups in the Formation of Some Biologically Important Lactams (Isatins) and their Further Derivatization

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