A green synthesis of isatoic anhydrides from isatins with urea–hydrogen peroxide complex and ultrasound

Deligeorgiev, Todor; Vasilev, Aleksey; Vaquero, Juan J.; Alvárez‐Builla, Julio

doi:10.1016/j.ultsonch.2006.12.003

Cited by 30 publications

(15 citation statements)

References 27 publications

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“…Our synthetic method simplifies isatin transformations considerably compared to prior methods. Synthesis of isatoic anhydride from isatin previously required using reagents such as peroxides 21,22 , phenyliodide 23 , and NBS 24 ; making benzamide derivatives from isatin required using chromic acid 25 , peroxide/phosphate buffer systems 26 , or in situ generated hydrazoic acid 27,14 ; and generating amino benzamide derivatives from isatoic anhydride required using ammonia 22,28 and ammonium carbonate 29 . In contrast, we can now approach multiple classes of derivatives from IAA using mild, established reactions.…”

Section: Mechanism Of Iaa Formationmentioning

confidence: 99%

Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide

Gondi

Bera

Westover

2019

Sci Rep

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Synthetic methods used to generate substituted anilines and quinazolines, both privileged pharmacological structures, are cumbersome, hazardous or, in some cases, unavailable. We developed a straightforward method for making isatoic anhydride-8-amide from isatin-7-carboxylic acid as a tool to easily produce a range of quinazoline and substituted aniline derivatives using adaptable pH-sensitive cyclization chemistry. The approaches are inexpensive, simple, fast, efficient at room temperature and scalable, enabling the synthesis of both established and new quinazolines and also highly substituted anilines including cyano derivatives.

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Section: Mechanism Of Iaa Formationmentioning

confidence: 99%

Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide

Gondi

Bera

Westover

2019

Sci Rep

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“…Isatoic anhydrides are generally used as intermediates in organic synthesis and lead to a wide variety of compounds and building blocks, most often anthranilic acids. A novel, fast and environmentally friendly sonochemical procedure for the oxidation of isatins has recently been reported by Deligeorgiev, et al [15]. The protocol entails the use of a urea-hydrogen peroxide complex in acetic or formic acid.…”

Section: Isatins Oxidationmentioning

confidence: 99%

Sonochemistry (Applications of Ultrasound in Chemical Synthesis and Reactions): A Review Part III

Mohamed

2019

JPRI

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As the need for friendly environment increasing the need for Sonochemistry increasing. Sonochemistry has become an important field of research for organic synthesis of diverse types of reactions, that decrease environmental hazardous and increase the yield of those reactions. The aim is to continue reviewing applications of ultrasound in chemical synthesis and reactions as reported in part I [1] and part II [2]. In this article I am trying to illustrate green sonochemical approaches for organic synthesis as one of the applications of ultrasound that minimize or eliminate the use and generation of hazardous substances and reduce environmental pollution.

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“…They are used in the manufacture of agricultural chemicals, dyes, pigments and corrosion inhibitors, as crosslinking agents and chain stoppers in resins in polymer and rubber chemistry. They have use also in the medicinal and pharmaceutical industries, as well as in cosmetics and perfumes production (Pummerer et al, 1940;Miyamae, 1940;Matos et al, 2003;Deligeorgiev et al, 2007). Isatoic compounds are also employed as intermediates in the organic synthesis of heterocyclic compounds, such as phthalimides, quinazolinones and benzimidazoles (Coppola, 1980;Kappe & Stadlbauer, 1981;Nawrot et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

The role of different nonspecific interactions and halogen contacts in the crystal structure organization of 5-chloroisatoic anhydride

et al. 2018

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The crystal structure of 6-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione (5-chloroisatoic anhydride), CHClNO, has been determined and analysed in terms of connectivity and packing patterns. The compound crystallizes in the noncentrosymmetric space group Pna2 with one molecule in the asymmetric unit. The role of different weak interactions is discussed with respect to three-dimensional network organization. Molecules are extended into one-dimensional helical arrangements, making use of N-H...O hydrogen bonds and π-π interactions. The helices are further organized into monolayers via weak C-H...O and lone pair-π interactions, and the monolayers are packed into a noncentrosymmetric three-dimensional architecture by C-Cl...π interactions and C-H...Cl and Cl...Cl contacts. A Hirshfeld surface (HS) analysis was carried out and two-dimensional (2D) fingerprint plots were generated to visualize the intermolecular interactions and to provide quantitative data for their relative contributions. In addition, tests of the antimicrobial activity and in vitro cytotoxity effects against fitoblast L929 were performed and are discussed.

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A green synthesis of isatoic anhydrides from isatins with urea–hydrogen peroxide complex and ultrasound

Cited by 30 publications

References 27 publications

Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide

Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide

Sonochemistry (Applications of Ultrasound in Chemical Synthesis and Reactions): A Review Part III

The role of different nonspecific interactions and halogen contacts in the crystal structure organization of 5-chloroisatoic anhydride

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