Synthesis of acyl azides from carboxylic acids using cyanuric chloride

Bandgar, B. P.; Pandit, S. S.

doi:10.1016/s0040-4039(02)00508-7

Cited by 76 publications

(28 citation statements)

References 18 publications

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“…[1][2][3][4][5][6][7] As for example, TCT and DMF (TCT-DMF adduct) have been used for chlorination of aliphatic alcohols, 8 but there have not been any elaborative studies about using such TCT-DMF adduct for chlorination of glycosyl substrates.…”

mentioning

confidence: 99%

A mild and general method for preparation of α-glycosyl chlorides

Chang

Chao

et al. 2009

Tetrahedron Letters

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confidence: 99%

A mild and general method for preparation of α-glycosyl chlorides

Chang

Chao

et al. 2009

Tetrahedron Letters

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“…33 and acyl azides. 34 In order to optimize the reaction conditions, at first the effect of different molar ratios of ROH/TT/n-Bu 4 our optimized conditions for the conversion of structurally different alcohols into their corresponding alkyl azides with 100% conversion (substrate consumption) which determined by GC. The results are shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

A Novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the 2,4,6-trichloro[1,3,5]triazine/n-Bu4NN3 system

Akhlaghinia¹,

Samiei²

2007

J. Braz. Chem. Soc.

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Alquil azidas são preparadas em bons a excelentes rendimentos, pelo tratamento de álcoois, tióis e trimetilsilil éteres com 2,4,6-tricloro[1,3,5]triazina/n-Bu 4 NN 3 em acetonitrila. Este método é altamente seletivo para conversão de álcoois primários a alquil azidas na presença de álcoois secundários e terciários, tióis e trimetilsilil éteres.Alkyl azides are prepared in good to excellent yields by treatment of alcohols, thiols and trimethylsilyl ethers with 2,4,6-trichloro[1,3,5]triazine/n-Bu 4 NN 3 in acetonitrile. This method is highly selective for conversion of primary alcohols to alkyl azides in the presence of secondary and tertiary alcohols, thiols and trimethysilyl ethers.

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“…Treatment of this acid with sodium azide by using cyanuric chloride in the presence of 4-methylmorpholine afforded labeled benzoyl azide in 80 % yield. [14] The benzoyl azide underwent thermal rearrangement in refluxing benzene to form the labeled phenyl isocyanate. [15] After completion of the reaction (GC), the phosphine catalyst [16] was added and the mixture was stirred at 65 8C for 3 h. The solvent was removed and the residue was distilled under reduced pressure to afford pure labeled diphenylcarbodiimide 5.…”

Section: Resultsmentioning

confidence: 99%

Novel Rhodium‐Catalyzed Reaction of Thiazolidine Derivatives with Carbodiimides

Zhou

Dong

Alper

2004

Chemistry A European J

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A new, simple, and regioselective synthesis of thiazolidinimine derivatives based on the rhodium-catalyzed reaction of readily available thiazolidines with carbodiimides is described. This methodology provides direct access to a large variety of thiazolidinimine derivatives, possibly via a novel regiospecific insertion of carbodiimides into one of two ring carbon-nitrogen bonds, as well as a metal-catalyzed imine elimination process.

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Synthesis of acyl azides from carboxylic acids using cyanuric chloride

Cited by 76 publications

References 18 publications

A mild and general method for preparation of α-glycosyl chlorides

A mild and general method for preparation of α-glycosyl chlorides

A Novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the 2,4,6-trichloro[1,3,5]triazine/n-Bu4NN3 system

Novel Rhodium‐Catalyzed Reaction of Thiazolidine Derivatives with Carbodiimides

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