Preparation of Tyrian Purple (6,6′-Dibromoindigo): Past and Present

Wolk, Joel L.; Frimer, Aryeh A.

doi:10.3390/molecules15085473

Cited by 20 publications

(10 citation statements)

References 187 publications

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“…Today, the compounds of Figure 3c can be produced in pure forms and in relatively large amounts following synthetic routes [20,[25][26][27]. Photographs of standard solutions of synthesized shellfish components are provided in Figure 3d.…”

Section: Biological Sources and Chemical Compositionmentioning

confidence: 99%

A Review on the Archaeological Chemistry of Shellfish Purple

Karapanagiotis

2019

Sustainability

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Shellfish purple, also known as Tyrian purple and royal purple, has a long history, which has been revealed and documented in recent years through valid physicochemical studies using sophisticated techniques. The aim of the work was to summarize the conclusions of these studies and to describe the results of two unpublished investigations regarding the (i) identification of shellfish purple in a textile (4th century BCE) from ancient Macedonia and (ii) dramatic effect of the dyeing conditions on the composition of the purple dye. Moreover, a critical discussion is included about the discovery of the shellfish pigment and dye based on the available scientific evidence. Previously published reports describing the identification of the shellfish colorant in objects of the cultural heritage were carefully summarized. Shellfish purple was not used only as colorant, but it served other purposes as emphasized in this review. In particular, examples for the use of shellfish purple in medicine, grave goods and fillers and plasters in walls, were described. Examples of materials and methods that were used in the past to produce “fake” purple, imitating the aesthetic result of the valuable royal marine material were summarized. Finally, the solubility of indigoids was discussed using modern approaches of physical chemistry.

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Section: Biological Sources and Chemical Compositionmentioning

confidence: 99%

A Review on the Archaeological Chemistry of Shellfish Purple

Karapanagiotis

2019

Sustainability

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“…It is not surprising, therefore, that there has been a significant and ever increasing interest in the design and synthesis of this class of heterocyles. 1‐(4‐chlorophenyl)ethanone 1 was treated with fuming HNO 3 and H 2 SO 4 to give 1‐(4‐chloro‐3‐nitrophenyl)ethanone 2 . Compounds 4a–c were obtained via the application of Ullmann condensation reaction on heating of 1‐(4‐chloro‐3‐nitrophenyl)ethanone 2 and 3a–c (2‐aminobenzoic acid, 2‐hydroxybenzoic acid, or 2‐mercaptobenzoic acid) with potassium carbonate, Cu, CuI, and nitrobenzene .…”

Section: Resultsmentioning

confidence: 99%

An Expedient Method for the Synthesis of 1,2,4‐Triazolo‐fused 1,5‐Benzodiazepine, 1,5‐Benzoxazepine, and 1,5‐Benzothiazepine Scaffolds: A Novel Seven‐membered Ring System of Biological Interest

Sharma¹,

Kishore

Singh

2018

Journal of Heterocyclic Chem

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New heterocyclic compounds 1‐(3‐methyl‐9H‐dibenzo[b,f][1,2,4]triazolo[4,3‐d][1,4]diazepin‐6‐yl)ethanone 8a, 1‐(3‐methyldibenzo[b,f][1,2,4]triazolo[4,3‐d][1,4]oxazepin‐6‐yl)ethanone 8b, and 1‐(3‐methyldibenzo[b,f][1,2,4]triazolo[4,3‐d][1,4]thiazepin‐6‐yl)ethanone 8c are synthesized from benzodiazepinone, benzoxazepinone, and benzothiazepinone derivatives. These heterocyclic scaffolds have wide medicinal importance. Best results were obtained in antibacterial screening against Escherichia coli, Enterobacter cloacae, and Staphylococcus aureus and antifungal screening against Candida albicans and Fusarium oxysporum. 1,1‐Diphenyl‐2‐picrylhydrazyl radical scavenging activities of compounds 6c, 7c, and 8c were tested in doses 10, 20, 30, 40, and 50 μg/mL and were expressed as IC50 values and percent of inhibition with means ± standard deviation of three different concentrations of synthesized compounds. The assignment of the structures of synthesized compounds was made by thin‐layer chromatography, elemental analysis, IR, 1H‐NMR, 13C‐NMR, and liquid chromatography–mass spectrometry.

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“…Topical studies examining the photoswitching abilities of N , N ’‐aryl‐substituted indigos pointed to a useful strategy to tailor their photochemical properties [7–9] . Synthetic routes towards 1 were developed by Baeyer and by Heumann and paved the way to multi‐ton production, yet its dibrominated counterpart 2 has never entered an industrial scale production [10] …”

Section: Methodsmentioning

confidence: 99%

Novel Arylindigoids by Late‐Stage Derivatization of Biocatalytically Synthesized Dibromoindigo

Schnepel

Dodero

Sewald

2021

Chemistry A European J

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Indigoids represent natural product-based compounds applicable as organic semiconductors and photoresponsive materials. Yetm odified indigo derivatives are difficult to access by chemicals ynthesis. Ab iocatalytic approach applying several consecutive selective CÀHf unctionalizations was developed that selectively provides access to variousi ndigoids:E nzymatic halogenation of ltryptophan followed by indole generation with tryptophanase yields 5-, 6-and 7-bromoindoles. Subsequent hydroxylation using af lavin monooxygenasef urnishes dibromoindigo that is derivatized by acylation.T his four-step one-pot cascade gives dibromoindigo in good isolated yields. Moreover,t he halogens ubstituent allows for late-stage diversification by cross-coupling directly performed in the crude mixture, thus enabling synthesis of a small set of 6,6'-diarylindigo derivatives. This chemoenzymatic approachp rovides am odular platform towards novel indigoids with attractive spectral properties.

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Preparation of Tyrian Purple (6,6′-Dibromoindigo): Past and Present

Abstract: Over the past century, various synthetic approaches have been suggested to the most famous dye of antiquity, Tyrian purple (6,6′-dibromoindigo). These synthetic routes have been exhaustively surveyed and critically evaluated from the perspective of convenience, cost, safety and yield.

Cited by 20 publications

References 187 publications

A Review on the Archaeological Chemistry of Shellfish Purple

A Review on the Archaeological Chemistry of Shellfish Purple

An Expedient Method for the Synthesis of 1,2,4‐Triazolo‐fused 1,5‐Benzodiazepine, 1,5‐Benzoxazepine, and 1,5‐Benzothiazepine Scaffolds: A Novel Seven‐membered Ring System of Biological Interest

Novel Arylindigoids by Late‐Stage Derivatization of Biocatalytically Synthesized Dibromoindigo

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