Cyanuric chloride, a useful reagent for macrocyclic lactonization

Венкатараман, К.; Wagle, D. R.

doi:10.1016/s0040-4039(00)92809-0

Cited by 55 publications

(25 citation statements)

References 7 publications

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“…For example, p-nitrobenzyl amide in the presence of cyanuric chloride is converted to p-nitrobenzonitrile [24]. Its use in the presence of triethylamine as an activation/cyclization agent for macrolactonization has also been reported [25].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Benzoxazinone Derivatives: A New Route to 2 (N Phthaloylmethyl)-4H-3,1-benzoxazin-4-one

Shariat

Abdollahi

2004

Molecules

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Abstract:A new method has been designed to prepare the known benzoxazinone derivative 2-(N-phthaloylmethyl)-4H-3,1-benzoxazin-4-one (4). The acyl chloride derivative N-phthaloylglycine reacts with anthranilic acid in chloroform, in the presence of triethylamine, to give an intermediate that is then reacted with cyanuric chloride, used as a cyclization agent, to produce the benzoxazinone derivative.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Benzoxazinone Derivatives: A New Route to 2 (N Phthaloylmethyl)-4H-3,1-benzoxazin-4-one

Shariat

Abdollahi

2004

Molecules

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“…1:1 dr ]; e) LiOH (30 equiv), dioxane:H 2 O (5:1), 80 °C, 6 h, 98% [ 31 + 31′ (not shown), ca. 1:1 dr ]; f) carboxylic acid activation methods (Corey– 22 Yamaguchi,23 cyanuric chloride,24 Mukaiyama salt,25 Shiina26); alcohol activation method (Mitsunobu21). …”

Section: Figuresmentioning

confidence: 99%

Total Synthesis of Sporolide B and 9-epi-Sporolide B

et al. 2010

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The total synthesis of the structurally unique secondary metabolite sporolide B (1b, Figure 1) is described. The total synthesis of 1b was developed on the basis of preliminary studies that revealed the reactivity of an appropriate o-quinone as a diene system toward a number of indene derivatives as dienophiles, first in intermolecular and thence intramolecular settings. Thus, substrates were devised (37, Scheme 5; 75, Scheme 11) that underwent exquisite intramolecular [4+2] cycloaddition reactions under thermal conditions to provide primitive sporolide-type structures that were subsequently elaborated to sporolide model system 4 (Figure 1), 9-epi-sporolide B (5, Figure 1), and sporolide B (1b). The requisite indene o-quinone precursor (75, Scheme 10) was synthesized through a rutheniumcatalyzed [2+2+2] cycloaddition reaction between a propargylic alcohol (42, Figure 8) and a chloroacetylenic cyclopentenyne (64, Scheme 9) followed by elaboration and silver-promoted oxidation of the resulting chloroindene derivative. In addition to the total synthesis of 1b, this work demonstrated, for the first time, the power of the intramolecular hetero [4+2] cycloaddition reaction in the total synthesis of complex molecules and the application of the ruthenium-catalyzed [2+2+2] cycloaddition reaction to highly substituted indene systems possessing a chlorine residue on the aromatic nucleus.

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“…One of the common applications of cyanuric chloride is the conversion of carboxyl groups into active esters for the preparation of nitrile, acyl azide, ester, amide, and acyl chloride from carboxylic acid derivatives [15,16]. Furthermore, cyanuric chloride is used to prepare alkyl chlorides from alcohols [17], amides from ketoximes [18], nitrile from aldoxime [19], isonitrile from formamide [20], disulfide from dimethylsulfoxide [21], and cyclic lactones [22]. In addition, the mixture of cyanuric chloride and dimethylformamide is used as a new organic reagent for the conversion of a broad sequence of secondary and primary alcohols to the corresponding alkyl chlorides and iodides [23,24].…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives under mild conditions using iminium cation from cyanuric chloride/dimethylformamide as a cyclizing agent

Shariat

Samsudin

Zakaria³

2013

Chemistry Central Journal

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BackgroundThe derivatives of 2-substituted 4H-3,1-benzoxazin-4-one belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial applications.ResultsA new and effective one-pot method for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives is described in this paper. By using the iminium cation from a mixture of cyanuric chloride and dimethylformamide as a cyclizing agent, a series of 2-substituted 4H-3,1-benzoxazin-4-one derivatives was synthesized in high yield under mild conditions and simple workup.ConclusionsThe iminium cation from a mixture of cyanuric chloride and N,N-dimethylformamide is an effective cyclizing agent for the room temperature one-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in high yields through a cyclodehydration reaction. Furthermore, the method was performed under mild conditions characterized by simplified pathways and workup, minimized energy, and fewer reaction steps, compared with the previous methods. The proposed method, which is a simpler alternative than the published methods, is applicable for the synthesis of other 2-substituted 4H-3,1-benzoxazin-4-one derivatives.

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Cyanuric chloride, a useful reagent for macrocyclic lactonization

Cited by 55 publications

References 7 publications

Synthesis of Benzoxazinone Derivatives: A New Route to 2 (N Phthaloylmethyl)-4H-3,1-benzoxazin-4-one

Synthesis of Benzoxazinone Derivatives: A New Route to 2 (N Phthaloylmethyl)-4H-3,1-benzoxazin-4-one

Total Synthesis of Sporolide B and 9-epi-Sporolide B

One-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives under mild conditions using iminium cation from cyanuric chloride/dimethylformamide as a cyclizing agent

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