Synthesis of 4,6-Dinitroindole From 2,4,6-Trinitrotoluene

Samet, A. V.; Zakharov, E. P.; Семенов, В. В.; Buchanan, A. C.; Gakh, Andrei A.

doi:10.1081/scc-100104054

Cited by 20 publications

(8 citation statements)

References 8 publications

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“…The indole-based extended amidine compounds of series 3 were too insoluble in aqueous media for kinetic studies of hydrolysis, so we studied the hydrolysis of the unsubstituted analogue 15 (Scheme 8). Compound 15 was prepared from 4,6-dinitroindole 35 employing the synthetic methodology shown in Scheme 5. The pH-rate profile shown in Figure 3 indicates the presence of two mechanisms for hydrolysis: the addition of water to protonated 15, 15H + (k 1 ), and the addition of water to diprotonated 15, 15H 2 2+ (k 2 ).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

The Synthesis of Vinylogous Amidine Heterocycles

LaBarbera

Skibo

2013

J. Org. Chem.

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We report herein a convenient synthetic methodology for the conversion of meta-dinitro heterocyclic rings to iminoquinones with vinylogous amidine functionality. These structures are found in nature, particularly in marine organisms, and may be important for the pigments and biological activity observed with such marine secondary metabolites. Using benzimidazole and indole ring systems we show the versatility of these vinylogous amidines for organic synthesis, including the following: transamination substitution reactions with virtually any primary amine, regional control of the substitution with substituents between the vinylogous amidine, and hydrolytic properties that can be controlled or optimized based on the properties of the chosen ring system. Taken together, this versatile chemistry and functionalization of organic molecules may be useful in the preparation of a variety of chemical products such as drug pharmacophores or assembling macromolecular structures.

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Section: ■ Results and Discussionmentioning

confidence: 99%

The Synthesis of Vinylogous Amidine Heterocycles

LaBarbera

Skibo

2013

J. Org. Chem.

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“…As indolines can be converted into indoles by oxidation 18 or by base-mediated elimination of an N -sulfonyl group 19 this is also a net Type 1 indole synthesis.…”

Section: Typementioning

confidence: 99%

Indole synthesis: a review and proposed classification

Taber

Tirunahari²

2011

Tetrahedron

674

194

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“…The same system has been used by Samet and co-workers in the synthesis of 4,6-dinitroindole from TNT [46], and Varma and collaborators have used it replacing the solvent by microwave irradiation [47].…”

Section: Reductionsmentioning

confidence: 99%

Recent Uses of Iron (III) Chloride in Organic Synthesis

Díaz¹,

Miranda²,

Padrón³

et al. 2006

COC

125

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Iron (III) chloride is extensively used in organic synthesis as an ideal Lewis acid since it is an inexpensive, efficient, stable, environmentally friendly and a convenient agent for several useful reactions such as; polymerisations, oxidations, oxidative couplings, reductions, C C bond formation, Ferrier rearrangement, one-pot multicomponent condensations, Friedel-Crafts reactions, cyclisations, glycosidation, Prins-type cyclisation, deprotection of various functional groups, and as a reagent in key steps of natural products synthesis. This comprehensive review attempts to cover the advances in this field, which have occurred in the last five years.

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Synthesis of 4,6-Dinitroindole From 2,4,6-Trinitrotoluene

Cited by 20 publications

References 8 publications

The Synthesis of Vinylogous Amidine Heterocycles

The Synthesis of Vinylogous Amidine Heterocycles

Indole synthesis: a review and proposed classification

Recent Uses of Iron (III) Chloride in Organic Synthesis

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