Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement

Lebel, H.; Leogane, Olivier

doi:10.1021/ol051428b

Cited by 120 publications

(50 citation statements)

References 33 publications

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“…For example, very recently a Curtius rearrangement of acyl azides has been developed by reaction of a carboxylic acid with ditert-butyl dicarbonate and sodium azide in the presence of tetrabutylammonium bromide and zinc(II) triflate, leading to Boc-amine [52].…”

Section: Miscellaneousmentioning

confidence: 99%

Recent Development about the Use of Pyrocarbonates as Activator in Organic Synthesis: A Review

Dalpozzo¹,

Bartoli²,

Bosco³

et al. 2009

COS

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In the last years, the use of pyrocarbonates and particularly di-tert-butyldicarbonate (Boc2O) has found a renaissance in organic synthesis. Together with the classical couple Boc2O/DMAP, new synthetic strategies have been developed in the presence of environmentally benign Lewis Acids. So new syntheses of protected Boc-amines and alcohols have appeared in literature. Moreover, the use as activator in the synthesis of esters and anhydrides has received attention from different research groups. Finally an interesting and unexpected synthesis of t-butyl ethers has appeared. This review aims to cover all the literature since 1998, but not the application to the synthesis of natural products.

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Section: Miscellaneousmentioning

confidence: 99%

Recent Development about the Use of Pyrocarbonates as Activator in Organic Synthesis: A Review

Dalpozzo¹,

Bartoli²,

Bosco³

et al. 2009

COS

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“…Carbamates have been accomplished by several methods including carbonization of amines or imines by chloroformate, [28,29] or oximinoacetoacetate [30], organic acids in the presence of azides [31,32], organic carbonate under solventfree conditions [33,34] and/or metal-mediated reductive acylation of nitriles [35] or oxime carbonates [36]. In the present work, reaction of the appropriate amine with ethyl chloroformate in different solvents (chloroform, THF, and DMF) at room temperature and higher temperatures in presence of amine (triethylamine) was tried but the low solubility of compounds 3a-e prevented the reactions from going forward.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides

et al. 2014

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KEYWORDSNew series of arylthiadiazole hydrazinecarboxamides (5a-e) have been synthesized by hydrazinolysis of carbamates (4a-e) and spectrally characterized. The new candidates have been screened for their anticonvulsant and immunomodulatory activities. Compound 5e was the most potent anticonvulsant candidate as it showed 100% protection against both maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) screens without neurotoxicity at 100 mg/kg (0.318 mmol/kg). With respect to immunomodulation, compounds 5a and 5d revealed immunostimulatory activity while compounds 5b, 5c, and 5e had immunosuppressive responses based on ELISA detection of IgM and IgG levels, counting the total mesenteric lymph nodes lymphocytes, and histo-pathological examinations.

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“…The carbamates were obtained in excellent yields (Scheme 139). Lebel and Leogane have reported [201] an efficient protocol for the preparation of tert-butyl carbamates 6 from the corresponding acid 162. The reaction of carboxylic acid 162 with di-tert-butyl dicarbonate 123 and sodium azide allowed the formation of an acyl azide 159, which undergoes a Curtius rearrangement in the presence of tetrabutylammonium bromide and zinc(II)triflate afforded the corresponding carbamates 6 through the trapping of isocyanate intermediate (Scheme 140).…”

Section: 7b Curtius Rearrangementmentioning

confidence: 99%

Recent Developments on the Carbamation of Amines

Chaturvedi

2011

COC

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Organic carbamates represent an important class of compounds showing various interesting properties. They find wide utility in various areas as pharmaceuticals, agrochemicals (pesticides, herbicides, insecticides, fungicides etc.), intermediates in organic synthesis, protection of amino group in peptide chemistry, and as linker in combinatorial chemistry etc. Classical synthesis of carbamates involves use of harmful reagents such as phosgene, its derivatives and carbon monoxide. Recently, various kinds of synthetic methods have been developed for the synthesis of organic carbamates. In the present review, I would like to highlight the recent developments on the synthesis of organic carbamates using variety of reagents.

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Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement

Cited by 120 publications

References 33 publications

Recent Development about the Use of Pyrocarbonates as Activator in Organic Synthesis: A Review

Recent Development about the Use of Pyrocarbonates as Activator in Organic Synthesis: A Review

Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides

Recent Developments on the Carbamation of Amines

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