Mono and dibromo-5,5-diethylbarbituric acids for cleavage of trimethylsilyl ethers

Khazaei, Ardeshir; Zolfigol, Mohammad Ali; Tanbakouchian, Zahra; Shiri, Morteza; Rostami, Amin; Iloukhani, H.

doi:10.1590/s0103-50532007000100028

Cited by 7 publications

(4 citation statements)

References 24 publications

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“…They have utilized these bromo compounds for the oxidative cleavage of different kinds of trimethylsilyl ethers in good yields at room temperature. 1662 1,2-Dibromoethane was utilized as a suitable reagent for the oxidative coupling of benzyl anions. 1663,1664 In this process, benzylic metalation of substituted toluenes was carried out using BuLi/KO-t-Bu/TMP(H) at the initial stage followed by C−C coupling in the presence of 1,2-dibromoethane as the oxidant.…”

Section: Oxidation Reactions Using Other Bromo-organic Compoundsmentioning

confidence: 99%

“…Khazaei et al prepared 1-bromo-5,5-diethylbarbituric acid and 1,3-dibromo-5,5-diethylbarbituric acid (Scheme ) by brominating the corresponding 5,5-diethylbarbituric acid in the presence of a base. They have utilized these bromo compounds for the oxidative cleavage of different kinds of trimethylsilyl ethers in good yields at room temperature …”

Section: Oxidation Reactionsmentioning

confidence: 99%

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Oxidation Reactions Using Other Bromo-organic Compoundsmentioning

confidence: 99%

Section: Oxidation Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…This compound is gaining widespread interest as a cheap and effective alternative to N-bromosuccinimide (19), and has wide ranging applications. Examples of its use in organic synthesis include: (i) the bromination of activated benzoic acids, [119] (ii) the solventfree oxidation of secondary alcohols, [120] and (iii) the oxidation of isoxazolines, [121] thiols, [122] and benzylic alcohols. [123] It has also used as an analytical reagent for the determination of numerous analgesics [124,125] and antihistamines.…”

Section: Nabr Bond Energies Of Selected Synthetically-important Molecmentioning

confidence: 99%

A dataset of highly accurate homolytic NBr bond dissociation energies obtained by Means of W2 theory

O'Reilly

Karton

2015

Int J of Quantum Chemistry

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Homolytic NBr bond dissociation constitutes the initial step of numerous reactions involving N‐brominated species. However, little is known about the strength of NBr bonds toward homolytic cleavage. We herein report accurate bond dissociation energies (BDEs) for a set of 18 molecules using the high‐level W2 thermochemical protocol. The BDEs (at 298 K) of the species in this set range from 162.2 kJ mol−1 (N‐bromopyrrole) to 260.6 kJ mol−1 ((CHO)2NBr). In order to compute BDEs of larger systems, for which W2 theory is not applicable, we have benchmarked a wide range of more economical theoretical procedures. Of these, G3‐B3 offers the best performance (root‐mean‐square deviations = 2.9 kJ mol−1), and using this method, we have computed NBr BDEs for four widely used N‐brominated compounds. These include (BDEs are given in parentheses): N‐bromosuccinimide (281.6), N‐bromoglutarimide (263.2), N‐bromophthalimide (274.7), and 1,3‐dibromo‐5,5‐dimethylhydantoin (218.2 and 264.8 kJ mol−1). © 2015 Wiley Periodicals, Inc.

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“…16 On the other hand, 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) (Scheme 1) is also a stable, commercially available and inexpensive heterocycle which has rarely utilized as a source of chlorine ion or radical in chlorination 17,18 or oxidation reactions. [19][20][21] To the best of our knowledge, there is no report of catalytic application of DCDMH and TCCA in the preparation of 1-thioacetamido-alkyl-2-naphthols.…”

Section: Introductionmentioning

confidence: 99%

Condensation of Aryl Aldehydes, 2‐naphthol, and Thioacetamide Catalyzed by N‐halo Reagents in Neutral Media

Khazaei

Abbasi

Moosavi‐Zare³

et al. 2015

J Chinese Chemical Soc

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A new three-component, highly efficient and solvent-free approach for the synthesis of known and new 1-thioamido-alkyl-2-naphthol derivatives was investigated. This was achieved via a one-pot condensation by reacting aryl aldehydes, 2-naphthol, and thioacetamide in the presence of catalytic amount of 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (TCCA) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH). Mechanistically, the in situ generation of Cl + ion from TCCA and DCDMH is proposed to catalyse the reactions in neutral media. In the presented work, most of the products have been reported for the first time.

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Mono and dibromo-5,5-diethylbarbituric acids for cleavage of trimethylsilyl ethers

Cited by 7 publications

References 24 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

A dataset of highly accurate homolytic NBr bond dissociation energies obtained by Means of W2 theory

Condensation of Aryl Aldehydes, 2‐naphthol, and Thioacetamide Catalyzed by N‐halo Reagents in Neutral Media

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